Potassium Carbonate → 6-Amino-3,4-dimethoxy-2-(2-pyridyl)benzonitrile

Participants

Reaction Steps

Under nitrogen, to anhydrous THF (1000 ml) was added 6-amino-2-iodo-3,4-dimethoxybenzonitrile (see Example 1, 50.0 g, 164 mmol), Pd(OAc)2 (1.85 g, 8.22 mmol), PPh3 (triphenylphosphine, 4.31 g, 16.4 mmol), THF wet boronate [from step (a), 286 g, 493 mmol], Cul (12.5 g, 65 mmol) and K2CO3 (45.5 g, 328 mmol). The reaction mixture was then stirred at reflux for 16 hours. After this time, the reaction mixture was cooled to room temperature and water (1000 ml) added. The mixture was then filtered through an Arbocel™ filter aid pad and the pad washed with THF (500 ml). The filtrate was then extracted with CH2Cl2 (1000 ml). The aqueous phase was back extracted with CH2Cl2 (500 ml) and the combined CH2Cl2 extracts were evaporated in vacuo to yield the crude product as a dark brown solid. Recrystallisation from EtOAc (250 ml) afforded 37.6 g (87%) of the title compound as a beige solid.

Provenance & Evidence