Water → HCID 54749376, compound

Participants

Reaction Steps

tert-Butyl 2-(2-(4-fluorophenyl)-7-hydroxy-4-methyl-5-oxo-4,5-dihydrothieno[3,2-b]pyridine-6-carboxamido)acetate. A mixture of ethyl 2-(2-bromo-7-hydroxy-4-methyl-5-oxo-4,5-dihydrothieno[3,2-b]pyridine-6-carboxamido)acetate (0.20 g, 0.48 mmol, Method 7), 4-fluorophenylboronic acid (0.134 g, 0.959 mmol, commercially available from Aldrich), Pd(Ph3)4 (0.055 g, 0.048 mmol) in 1,2-dimethoxyethane (4 mL) and aqueous Na2CO3 (2M, 0.72 mL) was heated under N2 at 100° C. for 2 hours. The suspension was cooled to room temperature, poured into water, extracted with CHCl3, dried over MgSO4 and evaporated. The residue was rinsed with Et2O and dried in vacuo to give the title compound. MS (ESI) m/z: Calculated 432.4; Observed; 431.1. 1H NMR (400 MHz, CDCl3) δ ppm 10.72-10.672 (1H, m), 7.53 (1H, s), 7.35-7.30 (2H, m), 7.14 (2H, t, J=8.5 Hz), 4.12 (2H, d, J=5.3 Hz), 3.23 (3H, s), 1.50 (9H, s).

Provenance & Evidence