6-Iodo-2,3-dimethoxypyridine → 5,6-Dimethoxypicolinonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,3-dimethoxy-6-iodopyridine (4-4, 24.0 g, 91 mmol) in DMF (181 mL) was added copper cyanide (9.73 g, 109 mmol) and heated to 150° C. for 20 minutes in a microwave reactor. The mixture was partitioned between saturated sodium carbonate and EtOAc three times. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The crude material was purified by gradient elution on silica gel (0 to 40% EtOAc in hexanes) to yield the desired product (4-5) as an off-white crystalline powder. ESI+MS [M+H]+ C8H8N2O2: 165.0 found, 165.1 required.

Provenance & Evidence