Potassium Phosphate, Tribasic → 4-Hydroxy-3-(2'-hydroxy-biphenyl-4-yl)-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-(4-bromo-phenyl)-4-hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester (100 mg, 0.25 mmol), 2-hydroxyphenylboronic acid (53 mg, 0.38 mmol), K3PO4 (169 mg, 0.63 mmol), P(o-tolyl)3 (7.7 mg, 2.5×10−5 mol), and Pd(OAc)2 (2.8 mg, 1.3×10−5 mol) was added THF (1.5 mL) and H2O (0.5 mL). The mixture was purged with nitrogen for 15 min., capped, and heated to 80° C. for 1.5 h. The reaction mixture was concentrated under reduced pressure and purified by reverse phase HPLC (0–70% CH3CN in NH4OAc aq.) to give the titled compound. MS (ESI) m/e 430 (M+Na)+, 408 (M+H)+; 406 (M−H)−. 1H NMR (300 MHz, DMSO-d6) δ 1.28 (t, J=7.12 Hz, 3H), 4.29 (q, J=7.01 Hz, 2H), 6.89 (td, J=7.46, 1.35 Hz, 1H), 6.96 (dd, J=8.14, 1.02 Hz, 1H), 6.99 (s, 1H), 7.17 (m, 1H), 7.30 (dd, J=7.46, 1.70 Hz, 1H), 7.46 (m, 2H), 7.54 (m, 2H), 9.56 (s, 1H), 12.21 (br s, 1H).

Provenance & Evidence