Acetic Acid → HCID 86662416, compound

Participants

Reaction Conditions

Reaction Steps

A sealable vial was charged with thieno[2,3-c]pyridin-5-yl trifluoromethanesulfonate (109 mg, 0.300 mmol), sodium acetate (75.3 mg, 0.900 mmol) and 1.0 M bromine in AcOH (0.900 mL, 0.900 mmol). The reaction was heated in a microwave reactor at 90° C. for 2 h. The reaction mixture was treated with aqueous Na2CO3 until the pH was >9, then extracted with EtOAc (3×20 mL). The combined extracts were washed with water (10 mL) and brine (10 mL), dried over MgSO4, and concentrated in vacuo. The residue was purified by ISCO chromatography (0 to 25% EtOAc:heptane) to afford 60 mg (55%) of the title compound as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.26 (d, J=0.4 Hz, 1 H), 8.61 (s, 1 H), 7.92 (d, J=1.2 Hz, 1H); MS (ESI): 362.08, 384.04 [M+H]+; HPLC tR=4.39 min (ZQ3: polar—5 min).

Provenance & Evidence