Nitrogen → HCID 67814872, compound

Participants

Reaction Conditions

Reaction Steps

To a resealable vial was added Pd(Ph3P)4 (20.33 mg, 0.018 mmol) and 4-fluorophenylboronic acid (49.2 mg, 0.352 mmol) before the vial was sealed and evacuated/backfilled with N2 (3×). To the vial was added 6-chloro-1-methyl-4-(trifluoromethyl)-4H-benzo[c]isoxazolo[4,5-e]azepine (52.9 mg, 0.176 mmol) dissolved in toluene (500 μL) and Na2CO3 (2M, 176 μl, 0.352 mmol). The solution was heated to 100° C. for 2 h before cooling to room temperature and diluting with water and EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford the titled compound (31.2 mg, 0.087 mmol). LC/MS m/z 361 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 7.88 (d, J=7.1 Hz, 1H), 7.77 (dt, J=1.7, 7.5 Hz, 1H), 7.52-7.41 (m, 4H), 7.29-7.21 (m, 2H), 5.38 (q, J=7.6 Hz, 1H), 2.56 (s, 3H).

Provenance & Evidence