Analyzing the synthesis route of 90924-06-4

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

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