Sodium Carbonate → 4-(5-fluoro-2-methoxyphenyl)-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a suspension of Example 3A (5 g, 14.79 mmol) in 2:1 1,2-dimethyoxyethane/ethanol (150 mL) was added 2M aqueous sodium carbonate (29.6 mL, 59.1 mmol), (5-fluoro-2-methoxyphenyl)boronic acid (3.02 g, 17.74 mmol) and dichlorobis(triphenylphosphine) palladium(II) (1.038 g, 1.479 mmol). The mixture was heated at 100° C. for 1.5 hours, cooled and diluted with 100 mL ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution, water, and brine, dried over magnesium sulfate, filtered, and concentrated. The residue was triturated with dichloromethane, filtered, and dried under vacuum. The filtrate was concentrated to ⅓ volume, and the solid filtered and rinsed with dichloromethane. The remainder of the filtrate was purified by flash chromatography on silica (Analogix 280) eluting with a gradient of 15 to 70% ethyl acetate/hexane. This was combined with the triturated material and dried over vacuum to give the title compound. MS (ESI+) m/z 383.5 (M+H)+.

Provenance & Evidence