Water → HCID 54689825, compound

Participants

Reaction Steps

To 4-hydroxy-3-(5-iodo-4-methylthien-2-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile (200 mg, 0.48 mmol, Example 222) and MgO (58.0 mg, 1.44 mmol) in dioxane (1.25 ml) and DMF (1.25 ml) was added H2O (0.530 ml) and the mixture was stirred for 10 min and then degassed with N2 for 2 min. 4-hydroxyphenylboronic acid (86 mg, 0.62 mmol), Cs2CO3 (344 mg, 1.06 mmol) and Pd(PPh3)4 (28.0 mg, 0.024 mm were added, the vessel flushed with N2, and then stirred at 80° C. for 2 h. The reaction was cooled to rt and overwhelmed with MeOH, filtered and the filtrate was concentrated to give a brown oil. The residue was taken up in DMSO: MeOH (1:1) and purified by reverse phase HPLC to give the title compound (98 mg, 0.26 mmol, 53%) as a light yellow solid MS (ESI) m/z 381.0 (M+H+); 1H NMR (300 MHz, DMSO-d6) δ ppm 7.51 (s, 3H), 7.28 (d, 1H), 6.83 (d, 1H), 6.79 (s, 1H), 4.09 (m, 1H), 2.22 (s, 1H) and 4-hydroxy-3-(4-methylthien-2-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile (Example 217) as a solid.

Provenance & Evidence