Pyridine → HCID 53913930, compound

Participants

Reaction Steps

A mixture of 0.6 g (2.75 mmol) of methyl 3-amino-4,7-dimethylindole-2-carboxylate, 0.22 ml (3.3 mmol) of pyridine and 15 ml of anhydrous THF was prepared. 10 ml of a solution of 0.26 ml (3.3 mmol) of methyl chloroformate in anhydrous THF was added dropwise at 0° C. over a period of 15 minutes and the reaction mixture was stirred for 1 hour. The reaction mixture was poured into 150 ml of ice water and extracted with 30 ml of ethyl acetate three times. The ethyl acetate layers were combined, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The solids thus obtained were recrystallized from ethyl acetate to provide 600 mg of red crystals. Yield: 79% m.p.: 184°-185° C.; 1H-NMR (300 MHz, DMSO-d6 /TMS; δppm): 8.64 (brs, 1H), 6.98 (d, 1H), 6.80 (d, 1H), 6.63 (brs, 1H), 3.92 (s, 3H), 3.79 (brs, 3H), 2.59 (s, 3H), 2.42 (s, 3H)

Provenance & Evidence