3-Chlorobenzamide → HCID 52913684, compound

Participants

Reaction Conditions

Reaction Steps

Compound 35 (59 mg, 0.20 mmol, 1.0 eq), 3-chlorobenzamide (46 mg, 0.30 mmol, 1.5 eq), NaOt-Bu (27 mg, 0.28 mmol, 1.4 eq), Pd(OAc)2 (2.2 mg, 0.0098 mmol, 0.050 eq) and Xantphos (11.4 mg, 0.0197 mmol, 0.100 eq) were dissolved in toluene (1 mL) in a microwave vial. The vial was purged with argon, capped, and heated at 110° C. for 18 h. After cooling the reaction was filtered over a plug of celite and the plug was washed with 5% MeOH/CH2Cl2. The solvents were removed in vacuo and the crude mixture was purified by flash chromatography on silica gel afforded 42 mg (57%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) δ 10.4 (s, 1H), 8.8 (s, 1H), 8.6 (s, 2H), 7.96 (t, J=1.8 Hz, 1H), 7.97-7.85 (m, 1H), 7.67-7.65 (m, 2H), 7.55 (t, J=7.8 Hz, 1H), 7.41 (t, J=1.9 Hz, 1H), 6.95 (t, J=2.0 Hz, 1H), 3.34 (s, 3H); [M+1]+: 373.1.

Provenance & Evidence