3-Chlorobenzamide → 3-Chloro-N-(6-chloro-4-(methyl(pyrimidin-5-yl)amino)pyridin-2-yl)benzamide

Participants

Reaction Conditions

Reaction Steps

Compound 14 (43 mg, 0.17 mmol, 1.0 eq), 3-chlorobenzamide (39 mg, 0.25 mmol, 1.5 eq), NaOt-Bu (23 mg, 0.24 mmol, 1.4 eq), Pd(OAc)2 (1.9 mg, 0.0085 mmol, 0.050 eq) and Xantphos (10 mg, 0.017 mmol, 0.10 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 21 mg (33%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) δ 10.95 (s, 1H), 9.12 (s, 1H), 8.89 (s, 2H), 8.00 (t, J=1.8 Hz, 1H), 7.89 (m, 1H), 7.63 (ddd, J=8.1, 1.2, 0.9 Hz, 1H), 7.58 (d, J=2.1 Hz, 1H), 7.50 (t, J=7.9 Hz, 1H), 6.66 (d, J=2.0 Hz, 1H), 3.39 (s, 3H); [M+1]+: 374.1.

Provenance & Evidence