Category: 90924-06-4

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.90924-06-4,1-Methyl-4-indolecarboxylic Acid,as a common compound, the synthetic route is as follows.

90924-06-4, To a stirred SOLUTION OF 4- [ (Z)- (4-BROMOPHENYL) (ethoxyimino) methyl]-1- (4-methyl-4- piperidinyl) piperidine (50 mg, 0.12 MMOL), 1-METHYL-1 H-indole-4-carboxylic acid (23 mg, 0.13 MMOL), and Et3N (24.3 mg, 0.24 MMOL) in DMF (2 mL), HATU (60.8 mg, 0.16 MMOL) was added at room temperature. After 16 h the mixture was poured into ice water (10 mL), and extracted with CH2CI2 (3X10 mL). The organic phase was dried over NA2SO4, and concentrated in vacuo. Purification by preparative TLC afforded title compound as a light YELLOW OIL. H NMR (CDCl3, 400MHz) 8 0.93 (s, 3H), 1.2 (t, 3H), 1.24-2. 2 (m, 11 H), 2.34-2. 46 (m, 1H), 2.76-2. 9 (m, 1 H), 2.9- 3.1 (m, 1H), 3.1-3. 3 (m, 1 H), 3.3-3. 7 (m, 2H), 3.78-3. 84 (s, 3H), 4.02-4. 18 (q, 2H), 6.4-6. 6 (m, 1H), 7.08-7. 14 (m, 4H), 7.19-7. 25 (m, 1H), 7.32-7. 36 (m, 1H), 7.48-7. 56 (m, 2H).

90924-06-4 1-Methyl-4-indolecarboxylic Acid 14987287, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; SCHERING AKTIENGESELLSCHAFT; WO2004/113323; (2004); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

90924-06-4, 1-Methyl-4-indolecarboxylic Acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

90924-06-4, [82] Into a 40-mL vial, was placed a solution of 1 -methyl- lH-indole-4-carboxylic acid (100 mg, 0.57 mmol, 1.00 eq.) in N,N-dimethylformamide (6 mL), HATU (325 mg, 0.86 mmol, 1.50 eq.), and DIEA (368 mg, 2.85 mmol, 5.00 eq.). After stirring for 1 h at 25 C, 4,5,6,7-tetrahydro-2H-indazol-3-amine hydrochloride (119.7 mg, 0.57 mmol, 1.00 eq.) was added. The resulting solution was stirred for 18 h at 25 C. The reaction mixture was diluted with water (40 mL), extracted with ethyl acetate (40 mL x3), washed with brine (100 mL x2), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The crude product was purified by Prep-HPLC with the following conditions: Column, XBridge Shield RP18 OBD Column, 5 um, 19×150 mm; mobile phase, water (0.1 %FA) and ACN (30.0% ACN up to 55.0% in 12 min); Detector, UV 254 nm to give two isomers. [83] Fraction A (Example 7): Rt=10.40 min; Yield: 15.4 mg (9%) as a light yellow solid. (ES, m/z) [M+H]+ : 295; iNMR (DMSO- 6, 400MHz,ppm): delta 7.65 (d, J= 8.0 Hz, 1H), 7.61-7.59 (m, 1H), 7.44 (d, J=2.8 Hz, 1H), 7.24-7.21 (m, lH), 6.49-6.48 (m, 1H), 6.40 (s, 2H), 3.84 (s, 3H), 2.36-2.30 (m, 4H), 1.69-1.66 (m, 4H).[84] Fraction B ( Example 8 ): Rt= 8.35 min; Yield: 21.2 mg (13%) as a white solid. (ES, m/z) [M+H]+ : 295; 1HNMR (DMSO- 6, 400MHz,ppm): delta 7.60 (d, J= 8.0 Hz, 1H), 7.49-7.47 (m, 1H), 7.39 (d, J=2.8 Hz, 1H), 7.21-7.18 (m, lH); 6.42-6.41 (m, 1H), 5.35 (s, 2H); 3.83-3.81 (m, 3H), 2.96-2.94 (m, 2H), 2.28-2.26 (m, 2H), 1.74-1.69 (m, 4H).

The synthetic route of 90924-06-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; THE ROCKEFELLER UNIVERSITY; PONDA, Manish, P.; BRESLOW, Jan, L.; SELNICK, Harold; EGBERTSON, Melissa; (207 pag.)WO2017/205296; (2017); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

90924-06-4, 1-Methyl-4-indolecarboxylic Acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,90924-06-4

General procedure: To a stirred solution of 25 (115 mg, 0.5 mmol) in DCM (10 mL) was added carboxylic acid (0.5 mmol), HOBT (68 mg, 0.5 mmol) and EDCI·HCl (144 mg, 0.75 mmol). The mixture was stirred at room temperature overnight, and washed successively with water (5 mL) and brine (10 mL × 2). The organic layer was dried over anhydrous Na2SO4, and concentrated to give the crude product, which was purified by flash chromatography (hexane/EtOAc = 3:1-1:1) afforded 4a-w.

90924-06-4 1-Methyl-4-indolecarboxylic Acid 14987287, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; Xia, Guangxin; You, Xiaodi; Liu, Lin; Liu, Haiyan; Wang, Jianfa; Shi, Yufang; Li, Ping; Xiong, Bing; Liu, Xuejun; Shen, Jingkang; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 1 – 10;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.90924-06-4,1-Methyl-4-indolecarboxylic Acid,as a common compound, the synthetic route is as follows.

90924-06-4, Oxalyl chloride (1.55 mL, 18.3 mmol) was added to a suspensionof the above acid (2.48 g, 15.3 mmol) in DCM (100 mL, anhydrous)and DMF (0.05 mL, 0.64 mmol) at 20 C. The mixture wasstirred at 20 C for 1 h to give a colourless solution which wascooled to 0 C. N,O-Dimethylhydroxylamine hydrochloride (1.64g, 16.8 mmol) and pyridine (3.71 mL, 45.9 mmol) were addedsequentially and the mixture was stirred at 20 C for 18 h, thenpartitioned between EtOAc and sat. aq. NaHCO3. Column chromatographywith 95:5 DCM:EtOAc gave N-methoxy-N-methylbenzofuran-5-carboxamide (2.28 g, 73%) as a pale brown oil. 1H NMR(CDCl3) d 7.99 (d, J = 1.4 Hz, 1H), 7.65-7.69 (m, 2H), 7.52 (dt, J =8.6, 0.6 Hz, 1H), 6.82 (dd, J = 2.2, 0.9 Hz, 1H), 3.56 (s, 3H), 3.39 (s,3H). Found: [M+H] = 206.2.

90924-06-4 1-Methyl-4-indolecarboxylic Acid 14987287, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; Sutherland, Hamish S.; Tong, Amy S.T.; Choi, Peter J.; Conole, Daniel; Blaser, Adrian; Franzblau, Scott G.; Cooper, Christopher B.; Upton, Anna M.; Lotlikar, Manisha U.; Denny, William A.; Palmer, Brian D.; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 1797 – 1809;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.90924-06-4,1-Methyl-4-indolecarboxylic Acid,as a common compound, the synthetic route is as follows.

Example 2.4: (S)-N-(3-(N.1-dimethyl-1H-indole-4-carboxamido)-4-phenylbutyl)-1- methyl-1H-benzord1imidazole-2-carboxamide1-Methyl-1 H-benzoimidazole-2-carboxylic acid ((S)-3-methylamino-4-phenyl-butyl)-amide hydrochloride (250 mg, 0.61 mmol), 1-methyl-1 H-indole-4-carboxylic acid (128 mg, 0.73 mmol), HOBt (112 mg, 0.73 mmol), EDC x HCI (176 mg, 0.92 mmol), and triethylamine (0.34 ml, 2.4 mmol) were dissolved in DCM (10 ml) and the reaction was stirred at rt over night. The mixture was diluted with EtOAc, washed with NaHC03- and NaCI-soln., dried (Na2S0 ), filtered and concentrated. The crude product was purified by chromatography (Flashmaster, heptane to EtOAc over 25 min; EtOAc for 10 min) to yield 191 mg (63%) of the title compound as off-white solid. [1 H-NMR (DMSO, 600 MHz, rotamers) 9.06/8.82 (br s, 1 H), 7.74-7.67 (m, 2H), 7.42-6.25 (m, 11H), 6.11/5.63 (s, 1H), 5.14/3.65 (br s, 1 H), 4.13/4.00 (s, 3H), 3.75/3.59 (s, 3H), 3.49-3.22 (m, 2H), 3.04/2.59 (s, 3H), 3.00-2.80 (m, 2H), 1.99-1.53 (m, 2H); LCMS RtA = 3.136 min; [M+H]+ = 494.2]., 90924-06-4

The synthetic route of 90924-06-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; NOVARTIS AG; BETSCHART, Claudia; COTESTA, Simona; HINTERMANN, Samuel; WAGNER, Juergen; ROY, Bernard, Lucien; GERSPACHER, Marc; VON MATT, Anette; BEHNKE, Dirk; WO2011/73316; (2011); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.90924-06-4,1-Methyl-4-indolecarboxylic Acid,as a common compound, the synthetic route is as follows.,90924-06-4

Example 11 O-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (113 mg), diisopropylethylamine (0.127 mL), and 4-dimethylaminopyridine in a catalytic amount were added to a mixture of N-cyclopropyl-5,6,7,8-tetrahydrocinnolin-6-amine monohydrochloride (56 mg), 1-methyl-1H-indole-4-carboxylic acid (52 mg), and DMF (2 mL) under an argon gas atmosphere, followed by stirring under heating for 60 hours at an oil temperature of 60 C., and then the resultant was cooled to room temperature. The reaction liquid was diluted with ethyl acetate and then washed with water (3 times) and saturated brine in this order, followed by drying, and concentrating under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol), thereby obtaining N-cyclopropyl-1-methyl-N-(5,6,7,8-tetrahydrocinnolin-6-yl)-1H-indole-4-carboxamide (9.3 mg).

As the paragraph descriping shows that 90924-06-4 is playing an increasingly important role.

Reference：
Patent; ASTELLAS PHARMA INC.; Kawakami, Shimpei; Sakurai, Minoru; Kawano, Noriyuki; Suzuki, Takayuki; Shiraishi, Nobuyuki; Hamaguchi, Wataru; Sekioka, Ryuichi; Moritomo, Hiroyuki; Motitomo, Ayako; US2014/249151; (2014); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

90924-06-4, 1-Methyl-4-indolecarboxylic Acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,90924-06-4

To a solution of 4-METHYL-4- [ (3S)-3-METHYL-4- [ (1 R)-1- [4- (TRIFLUOROMETHYL) PHENYL] ETHYL] PIPERAZIN-1-YL]-1-PIPERIDINECARBOXYLIC ACID-DIMETHYLETHYL ester (127 mg, 0.27 MMOL) in CH2CI2 (3 mL) was added trifluoromethyl acetic acid (1.5 mL) at room temperature. After 2h the reaction mixture was concentrated in vacuo, and dried under vacuum for 3 h. Re-dissolved the product in DMF (5 mL), then 1-methyl-1 H-indol-4-carboxylic acid (52 mg, 0.30 MMOL), Et3N (55 mg, 0.54 MMOL), and HATU (134 mg, 0.35 MMOL) was added successively at room temperature. After 16 h the reaction mixture was poured into ice water (10 mL), and the mixture was extracted with EtOAc (3X20 mL). The organic phase was washed with NAHCO3 (10 mL, sat. ) and brine (10 mL), and dried over NA2SO4. Concentration in vacuo, and purification by column chromatography (CH2CI2-MEOH, 9: 1) afforded the title compound as a yellow solid. MS: 526 (M+).’H NMR (CDCl3, 400MHZ) : S : 0.9 (s, 3H), 1.14 (d, 3H), 1.3 (d, 4H), 1.4-1. 8 (m, 2H), 1.82-2. 05 (m, 1H), 2.18-2. 8 (m, 6H), 2.9-3. 1 (m, 1H), 3.1-3. 3 (m, 1H), 3.3-3. 7 (m, 2H), 3.8 (s, 3H), 3.9-4. 3 (m, 2H), 6.48 (m, 1H), 7.05-7. 16 (m, 2H), 7. 18-7. 28 (M, 1 H), 7.3-7. 38 (m, 1 H), 7.46-7. 6 (m, 4H).

As the paragraph descriping shows that 90924-06-4 is playing an increasingly important role.

Reference：
Patent; SCHERING AKTIENGESELLSCHAFT; WO2004/113323; (2004); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles