3-Chlorobenzamide → HCID 51037931, compound

Participants

Reaction Conditions

Reaction Steps

Compound 3 (944 mg, 4.55 mmol, 1.00 eq), 3-chlorobenzamide (1.06 g, 6.81 mmol, 1.50 eq), NaOt-Bu (612 mg, 6.37 mmol, 1.40 eq), Pd(OAc)2 (51 mg, 0.23 mmol, 0.050 eq) and Xantphos (263 mg, 0.455 mmol, 0.100 eq) were dissolved in toluene (9.4 mL) in a flame-dried sealed tube and heated at 110° C. for 18 h. The reaction was cooled to rt, diluted with CH2Cl2 and filtered through a plug of celite. Purification by flash chromatography on silica gel afforded 1.08 g (73%) of the title compound as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 11.07 (s, 1H), 9.17 (s, 1H), 8.59 (d, J=2.7 Hz, 1H), 8.46 (dd, J=4.7, 1.2 Hz, 1H), 8.33 (s, 1H), 8.00 (t, J=1.8 Hz, 1H), 7.89 (d, J=7.8 Hz, 1H), 7.77 (ddd, J=8.4, 2.8, 1.4 Hz, 1H), 7.67-7.64 (m, 1H), 7.54-7.48 (m, 2H); ES-MS [M+1]+: 327.1.

Provenance & Evidence