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

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Reaction Conditions

Reaction Steps

3-Amino-1-(4-methoxy-benzyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid methyl ester (200 mg, 0.64 mmol) was dissolved in toluene (6 mL), to which Cs2CO3 (417 mg, 1.28 mmol) and trifluoro-methanesulfonic acid 2-fluoro-4-trimethylsilanyl-phenyl ester (263 mg, 0.83 mmol) were added and the mixture degassed with nitrogen before addition of Pd2dba3 (29 mg, 0.032 mmol) and Xantphos (37 mg, 0.064 mmol). The mixture was heated at 105° C. for 18 hours, allowed to cool to ambient temperature then partitioned between EtOAc (50 mL) and water (30 mL). The organic layer was isolated, dried (Na2SO4), filtered and evaporated to give a black oil. The oil was purified by flash column chromatography on silica (Si-PPC, cyclohexane:EtOAc, gradient 90:10 to 40:60) to provide the title compound as a pale brown solid (269 mg, 88%). LCMS (method B): RT=2.81 min, M+H+=478.

Provenance & Evidence