Tetrahydrofuran → HCID 592582, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of potassium carbonate (1.48 g, 10.7 mmol), phenylboronic acid (645 mg, 5.29 mmol), 3-chloro-4-iodonitro benzene (1.00 g, 3.53 mmol), and THF (31 ml) was degassed with nitrogen in a sealable tube for 10 min. The dichloromethane adduct of 1,1′-bis(diphenylphosphino)ferrocene]dichloro palladium (351 mg, 0.429 mmol) was added to the reaction mixture and the pressure tube was sealed. The reaction mixture was stirred at 100° C. for 42 h. The mixture was cooled to 23° C., diluted with DCM (40 ml), and filtered. The filtrate was concentrated. The residue was purified by FCC (3-50% EtOAc/hexanes) to yield the titled compound (796 mg, 97%). 1H NMR (600 MHz, DMSO-d6): 8.42-8.41 (m, 1H), 8.26 (dd, J=8.5, 2.2, Hz 1H), 7.72 (d, J=8.5 Hz, 1H), 7.55-7.48 (m, 5H).

Provenance & Evidence