Methanol → 1H-Pyrrolo[2,3-B]pyridine-5-carboxylic acid, 1-[(4-methylphenyl)sulfonyl]-, methyl ester

Participants

Reaction Steps

Under N2 purge, 5-Bromo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (1.0 g, 2.8 mmol), Et3N (0.75 mL, 5.4 mmol), Pd(OAc)2 (64 mg, 0.28 mmol), Ph3P (0.45 g, 1.7 mmol) and MeOH (5.0 mL, 120 mmol) were loaded in 20 mL DMF. The vessel was purged with CO 5 minutes and fixed with a condenser tube with CO balloon. The reaction was heated to 100 C for 6 hours and monitored by TLC (rf 5-Bromo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine=0.72, rf 1-(Toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid methyl ester=0.43, CH2Cl2). After 6 hours, the reaction was removed from heat, diluted to 100 mL with water and extracted with EtOAC (100 mL). The phases were separated and organic was washed with additional water (2×100 mL) and brine (1×100 mL), dried over Na2SO4, filtered, and dried in vacuo. The resulting yellow powder was purified over a short plug of silica gel with CH2Cl2 until all material was recovered. Yield 0.94 g, white powder.

Provenance & Evidence