Sodium Methoxide → (S)-7-bromo-3-chloro-1-methoxy-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-oxazol]-2'-amine

Participants

Reaction Conditions

Reaction Steps

A 100 mL RBF containing a solution of (S)-7-bromo-3-chloro-1-fluoro-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine (0.50 g, 1.30 mmol, prepared as described in Method BB33) in methanol (13 mL) was treated with sodium methoxide (0.36 mL, 6.50 mmol) and the resulting suspension was heated to 65° C. for 3 h on a hot-plate. The reaction was cooled to RT and concentrated to dryness under high vacuum. The resulting yellowish residue was taken up in dichloromethane (75 mL), water (25 mL), and the organic layer was separated. The organic layer was dried over sodium sulfate and concentrated to yield the crude product. The crude product was purified by silica gel flash column chromatography and eluted using DCM/MeOH gradient to provide (S)-7-bromo-3-chloro-1-methoxy-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine as an amorphous off-white solid. [MS: m/z=395.9 (M+H)].

Provenance & Evidence