Category: 343-90-8

343-90-8, 1-(5-Fluoro-1H-indol-3-yl)-N,N-dimethylmethanamine is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 46: Intermediate 47–Diethyl [ (5-fluoro-lH-indol-3-yl) methyl] (methyl) malonate [0431] A solution of 5-fluorogramine (15. 5g, 80. 6MMOL) in acetonitrile (450mL) was treated with diethyl methylmalonate (20. 8mL, 121MMOL) and tributylphosphine at reflux for 17 hours. The cooled reaction is concentrated under reduced pressure and dissolved in ethyl acetate (1. 5L), washed with 1N aqueous HC1 (500ML), saturated aqueous NaCl (500ML), dried over MgS04 and concentrated under reduced pressure to an orange oil. Chromatography ( (3 : 1) hexane-EtOAc) afforded 16. 5g (64%) of desired product as an oil which solidifies on standing to a white solid: mp 76-77 C., 343-90-8

As the paragraph descriping shows that 343-90-8 is playing an increasingly important role.

Reference：
Patent; WYETH; WO2005/12291; (2005); 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.343-90-8,1-(5-Fluoro-1H-indol-3-yl)-N,N-dimethylmethanamine,as a common compound, the synthetic route is as follows.

A. 5-Fluoroindole-3-acetonitrile A mixture of 38 g of 3-dimethylaminomethyl-5-fluoroindole (0.198 mole; cf. Hoffman et al. J. Heterocyclic Chem. 2, 298 (1965); of the 5-fluorogramine therein) in 500 ml of methanol was prepared. Then a solution of 25.7 g of KCN (0.396 mole) in 50 ml of water was added, with stirring. The stirred mixture was cooled to 20 C. and 34.6 ml of methyl iodide (0.556 mole) was added over a 20 minute period. The mixture was then stirred at about 20 C. for 16 hours. The solvent was removed by evaporation and the residue was partitioned between ether and water. The ether portion was washed with water, 5% HCl, saturated NaHCO3 solution, water, and brine, dried over MgSO4 and evaporated to leave a liquid residue. This residue was distilled at reduced pressure in a Kugelrohr apparatus. The fraction distilling at 134-140 C. and 0.3 to 0.1 Torr was collected and crystallized from ethyl acetate-petroleum ether, mp 58-59, yield 5.3 g (44%).

343-90-8, The synthetic route of 343-90-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Miles Laboratories, Inc.; US4283336; (1981); A;,
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

343-90-8, 1-(5-Fluoro-1H-indol-3-yl)-N,N-dimethylmethanamine is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A. 5-Fluoroindole-3-acetonitrile A mixture of 38 g of 3-dimethylaminomethyl-5-fluoroindole (0.198 mole; cf. Hoffman et al. J. Heterocyclic Chem. 2, 298 [1965]; of the 5-fluorogramine therein) in 500 ml of methanol was prepared. Then a solution of 25.7 g of KCN (0.396 mole) in 50 ml of water was added, with stirring. The stirred mixture was cooled to 20 C. and 34.6 ml of methyl iodide (0.556 mole) was added over a 20 minute period. The mixture was then stirred about 20 C. for 16 hours. The solvent was removed by evaporation and the residue was partitioned between ether and water. The ether portion was washed with water, 5% HCl, saturated NaHCO3 solution, water, and brine, dried over MgSO4 and evaporated to leave a liquid residue. This residue was distilled at reduced pressure in a Kugelrohr apparatus. The fraction distilling at 134-140 C. and 0.3 to 0.1 Torr was collected and crystallized from ethyl acetate-petroleum ether, mp. 58-59, yield 5.3 g (44% theory)., 343-90-8

Big data shows that 343-90-8 is playing an increasingly important role.

Reference：
Patent; Miles Laboratories, Inc.; US4283410; (1981); A;,
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.343-90-8,1-(5-Fluoro-1H-indol-3-yl)-N,N-dimethylmethanamine,as a common compound, the synthetic route is as follows.

General procedure: To a solution of gramine[1] (8.00 mmol) and AcOH (114 muL, 2.00 mmol) in THF (10 mL) a solution of dimethylsulphate (3.79 mL, 40 mmol) and AcOH (114 muL, 2.00 mmol) in THF (8 mL) was added at 0 C dropwise. After stirringfor 1 h, Et2O (40 ml) was added and the reaction mixture was cooled to -18 C, precipitates were filtered, washed with Et2O (3*30 mL), dried over P2O5 in vacuum to afford gramine methosulfate derivative., 343-90-8

Big data shows that 343-90-8 is playing an increasingly important role.

Reference：
Article; Reinfelds, Matiss; Kalinins, Konstantins; Katkevica, Dace; Zemribo, Ronalds; Katkevics, Martins; Tetrahedron Letters; vol. 56; 43; (2015); p. 5882 – 5885;,
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

343-90-8, 1-(5-Fluoro-1H-indol-3-yl)-N,N-dimethylmethanamine is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a stirred mixture of S1 (R = H, F, Br, or OMe; 5.20 mmol) and diethyl malonate (4.85 mmol) in Et2O (2.6mL) was added dropwise ethyl propiolate (5.20 mmol) at room temperature. The mixture was stirred for 45 min atthis temperature, followed by quenching with H2O. The whole was extracted with Et2O. The extract was washedsuccessively with H2O and brine, and dried over MgSO4. The filtrate was concentrated under reduced pressure togive an oily residue, which was purified by flash chromatography over silica gel with n-hexane-EtOAc (8:1) togive the corresponding S2 as a pale yellow needle., 343-90-8

The synthetic route of 343-90-8 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Iwata, Akira; Inuki, Shinsuke; Oishi, Shinya; Fujii, Nobutaka; Ohno, Hiroaki; Tetrahedron; vol. 71; 37; (2015); p. 6580 – 6585;,
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.343-90-8,1-(5-Fluoro-1H-indol-3-yl)-N,N-dimethylmethanamine,as a common compound, the synthetic route is as follows.

Example 167; 2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid [5-fluoro-3- (2-pyridin-3-yl- ethyD-indol-l-yli- amide; Step 1 : A solution of 5-fluorogramine (576 mg, 3 mmol) and pyridine-3-carboxaldehyde (531 mg, 3 mmol) in MeCN (6 mL) is treated with Bu3P (1.12 mL, 4.5 mmol) and stirred at 900C for 24 h. The mixture is concentrated, filtered through a pad of silica gel eluting with 30% EtOAc in heptane to afford 5-fluoro-3-(2-pyridin-3-yl-vinyl)-lH-indole as a mixture of olefin isomers, which is used in the next step without further purification., 343-90-8

As the paragraph descriping shows that 343-90-8 is playing an increasingly important role.

Reference：
Patent; SANOFI-AVENTIS; WO2008/121670; (2008); 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