Sodium Carbonate → 3-[6-(1-Hydroxyethyl)pyridin-3-yl]-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}benzoic acid

Participants

Reaction Steps

A mixture of 1-(5-bromopyridin-2-yl)ethanol (40.3 mg, 0.199 mmol), 3-(dihydroxyboranyl)-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}benzoic acid (31.8 mg, 0.072 mmol), PdCl2(dppf) (11.9 mg, 0.016 mmol), sodium carbonate (2 M, 0.15 mL, 0.300 mmol) and DMF (2 mL) was flushed and purged with Ar(g) (3×) and irradiated in a microwave reactor for 15 minutes at 120° C. The mixture was filtered and was directly purified by reverse phase HPLC to afford 3-[6-(1-hydroxyethyl)pyridin-3-yl]-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}benzoic acid (26.7 mg, 0.052 mmol, 71.4%). MS APCI C19H16F3N4O3 [M+H]+ 405. found 405. 1H NMR (500 MHz, DMSO-d6) δ13.1 (s, 1H), 10.54 (s, 1H), 8.88 (d, J=5.1 Hz, 1H), 8.77 (s, 1H), 8.38 (d, J=7.9 Hz, 2H), 8.15 (d, J=8.0 Hz, 1H), 7.86 (s, 1H), 7.68 (d, J=8.0 Hz, 1H), 7.34 (d, J=5.1 Hz, 1H), 4.82 (q, J=6.0 Hz, 1H), 1.41 (d, J=6.0 Hz, 3H).

Provenance & Evidence