Cesium carbonate → HCID 68095273, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(7-bromoisoquinolin-3-yl)cyclopropanecarboxamide (200 mg, 0.68 mmol), 4-chloro-2-methylphenylboronic acid (138.72 mg, 0.816 mmol), cesium carbonate (268 mg, 0.816 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (25 mg, 0.05 eq) in acetonitrile/water (10 mL, 10:1) was stirred at 130° C. under microwave irradiation for 30 min under nitrogen. The reaction mixture was diluted with ethyl acetate (20 mL) and filtered. The solid was washed with ethyl acetate (20 mL×4). The organic layer was combined, dried over sodium sulfate, filtered and concentrated. The crude product was purified by prep-HPLC to give the desired product (94.6 mg, 41.3%). LCMS (ESI): RT (min)=1.328, M+H+=336.8, method=A. 1H NMR (400 MHz, DMSO-d6) δ 10.95 (s, 1H), 9.16 (s, 1H), 8.49 (s, 1H), 7.99 (s, 1H), 7.92 (d, J=8.4 Hz, 1H), 7.68 (dd, J=1.6, 8.4 Hz, 1H), 7.48-7.34 (m, 3H), 2.28 (s, 3H), 2.07-2.05 (m, 1H), 0.86-0.82 (m, 4H).

Provenance & Evidence