Cesium carbonate → methyl 6-methyl-4-(p-tolyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

Participants

Reaction Steps

A solution of methyl 6-amino-5-formyl-2-methyl-4-(p-tolyl)nicotinate (2.45 g, 8.62 mmol) and Cs2CO3 (5.62 g, 17.23 mmol) in methanol (70 ml) was treated with TMS-diazomethane (2M in hexane) (17.23 ml, 34.5 mmol) dropwise at 60° C. The mixture was stirred at 60° for 1 hour, cooled to rt, quenched with sat NH4Cl, extracted with EtOAc, washed with water, Brine, dried with Na2SO4, filtered, and concentrated to afford methyl 6-methyl-4-(p-tolyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (2.15 g, 7.67 mmol, 89% yield): 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.86 (br. s., 1 H), 7.40 (d, J=8.1 Hz, 2 H), 7.31-7.26 (m, 3 H), 6.43 (dd, J=2.0, 3.5 Hz, 1 H), 3.64 (s, 3 H), 2.71 (s, 3 H), 2.43 (s, 3 H); LCMS (m/z) ES+=281 (M+1).

Provenance & Evidence