Sodium Bicarbonate → HCID 58233790, compound

Participants

Reaction Steps

4,4-Difluorospiro[cyclohexane-1,2′-pyrano[2,3-b]pyridine] (87) DAST (0.36 ml, 2.7 mmol) was added to a stirred ice-cooled solution of 4H-spiro[cyclohexane-1,2′-pyrano[2,3-b]pyridin]-4-one (85) (0.29 g, 1.3 mmol) in DCM (30 mL) under N2. The resulting mixture was allowed to warm up to rt and stirred at ambient temperature for 21 h. The mixture was poured into ice and saturated NaHCO3 aqueous solution and extracted with DCM (2×). The combined organics were washed with brine, dried over Na2SO4, and concentrated in vacuo to give a 2; 1 mixture of 4,4-difluorospiro[cyclohexane-1,2′-pyrano[2,3-b]pyridine] (87) and 4-fluorospiro[cyclohex-3-ene-1,2′-pyrano[2,3-b]pyridine] (88) (0.25 g, 80% yield). This material was taken onto the next step without separation. LCMS-ESI (POS), M/Z, M+1: Found 238.1.

Provenance & Evidence