Pyridine → HCID 86689037, compound

Participants

Reaction Steps

A mixture of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (5.6 g, 20.0 mmol), 3-nitrophenylboronic acid (5.0 g, 30.0 mmol), Cu(OAc)2 (3.6 g, 20.0 mmol), pyridine (9.5 g, 120.0 mmol) and 4 Å MS (10.0 g) in dry DCM (150 mL) was purged with O2 before stirred at r.t. for 5 days. The reaction mixture was filtered through a celite pad and the filter cake was thoroughly washed with DCM. The filtrate was concentrated and purified by column chromatographic (silica gel, 0 to 50% DCM in PE during 15 min and then 0 to 20% ethyl acetate in a mixture of PE & DCM (1:1)) to afford 4-chloro-5-iodo-7-(3-nitrophenyl)-7H-pyrrolo[2,3-d]pyrimidine (16) (6.6 g, 82% yield) as a white solid. LC-MS (ESI): m/z (M/M+2) 399.9/400.9.

Provenance & Evidence