3-Chlorobenzamide → HCID 50992438, compound

Participants

Reaction Conditions

Reaction Steps

Compound 13 (580 mg, 2.31 mmol, 1.00 eq), 3-chlorobenzamide (539 mg, 3.46 mmol, 1.50 eq), NaOt-Bu (311 mg, 3.24 mmol, 1.40 eq), Pd(OAc)2 (26 mg, 0.12 mmol, 0.050 eq) and Xantphos (134 mg, 0.232 mmol, 0.100 eq) were dissolved in toluene (6 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 68 mg (9%) of the title compound as an off white semi-solid: 1H NMR (400 MHz, DMSO-d6) δ 10.44 (s, 1H), 9.03 (s, 1H), 8.68 (s, 2H), 7.97 (t, J=1.6 Hz, 1H), 7.88 (d, J=7.8 Hz, 1H), 7.65 (t, J=9.8 Hz, 2H), 7.59 (t, J=2.0 Hz, 1H), 7.56 (t, J=7.8 Hz, 1H), 7.42 (t, J=8.2 Hz, 1H), 6.91 (dd, J=8.1, 1.9 Hz, 1H); ES-MS [M+1]+: 326.1.

Provenance & Evidence