Cesium carbonate → 3-(2-Fluoro-4-trimethylsilanyl-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester

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Reaction Steps

3-Amino-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (25 g, 114 mmol), trifluoro-methanesulfonic acid 2-fluoro-4-trimethylsilanyl-phenyl ester (47.0 g, 149 mmol), Pd2(dba)3 (5.0 g, 5.5 mmol), Xantphos (6.5 g, 11.3 mmol) and cesium carbonate (74.5 g, 228 mmol) were suspended in toluene (500 mL) and the flask evacuated and purged with argon. The reaction mixture was heated at reflux for 18 hours. The mixture was cooled and filtered through Celite® washing through with toluene. The filtrate was evaporated in vacuo and the residue subjected to flash chromatography (SiO2, gradient 0-10% MeOH in DCM) to give the title compound (37.4 g, 85%) as a yellow solid. 1H NMR (CDCl3) 8.79 (1H, d, J=1.1 Hz), 8.39 (1H, d, J=6.1 Hz), 7.60 (1H, s, br), 7.25 (0.5H, s), 7.22 (1H, s), 7.21 (0.5H, d, J=1.0 Hz), 7.14-7.10, (2H, m), 4.42 (2H, q, J=7.0 Hz), 3.97 (3H, s), 1.44 (3H, t, J=7.0 Hz), 0.26 (9H, s).

Provenance & Evidence