3-Chlorobenzamide → HCID 58337495, compound

Participants

Reaction Conditions

Reaction Steps

Compound 11 (1.0 g, 3.5 mmol, 1.0 eq), 3-chlorobenzamide (820 mg, 5.27 mmol, 1.50 eq), NaOt-Bu (473 mg, 4.92 mmol, 1.40 eq), Pd(OAc)2 (40 mg, 0.18 mmol, 0.050 eq) and Xantphos (203 mg, 0.351 mmol, 0.100 eq) were dissolved in toluene (15 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 921 mg (73%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) δ 10.5 (s, 1H), 8.47 (d, J=2.8 Hz, 1H), 8.45 (dd, J=4.6, 1.3 Hz, 1H), 7.95 (t, J=1.8 Hz, 1H), 7.86 (dt, J=7.8, 1.3 Hz, 1H), 7.77 (t, J=1.8 Hz, 1H), 7.67 (dq, J=8.1, 1.2 Hz, 1H), 7.58 (ddd, J=8.4, 2.9, 1.4 Hz, 1H), 7.56 (t, J=7.9 Hz, 1H), 7.49 (dd, J=8.4, 4.7, 1H), 7.40 (t, J=2.1 Hz, 1H), 6.94 (t, J=2.1 Hz, 1H); [M+1]+: 359.2.

Provenance & Evidence