HCID 54689858, compound → HCID 54689877, compound

Participants

Reaction Conditions

Reaction Steps

The 3-(4-benzyloxy-3,5-dibromo-phenyl)-4-hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile from Example 36e (150 mg, 0.281 mmol) was dissolved in 30% HBr/AcOH (2 mL) and sealed in a reaction tube with stirring for 30 min at 70° C. The reaction is cooled to room temperature and concentrated in vacuo. The resulting solid is washed with Et2O and filtered, then placed under high vacuum to remove remaining acid. The solid is then taken up in NH4OH (2 mL) and stirred at room temperature for 20 minutes. The reaction mix is concentrated and taken up in 1M HCl. The resulting solid is filtered and rinsed with water to give 75 mg of a green solid as the titled compound (0.169 mmol, 60% yield). 1H NMR (300 MHz, DMSO-d6) δ 12.54 (bs, 1H), 9.98 (bs, 1H), 7.59 (s, 2H), 7.09 (s, 1H), 4.13 (bs, 1H). MS (ESI APCI) m/e 442 (M+H)+; 440 (M−H)−.

Provenance & Evidence