Tetrahydrofuran → HCID 67112718, compound

Participants

Reaction Conditions

Reaction Steps

To a thick slurry of p-methylbenzenesulfonylhydrazine (0.036 g, 0.19 mmol) and 3-(2-(2-fluoro-4-methylphenyl)thiazolo[5,4-b]pyridine-5-yl)-3-phenylcyclobutanone (0.050 g, 0.13 mmol) in 0.3 mL MeOH under nitrogen was added a pre-mixed suspension of sodium cyanoborohydride (0.016 g, 0.26 mmol) and zinc chloride, 0.5 M solution in THF (0.26 mL, 0.13 mmol) in 0.26 mL MeOH, via pipette. The reaction mixture was sealed and heated to 70° C. for 3 h. The reaction mixture was adsorbed onto 600 mg silica gel and dried. Purification by silica gel chromatography, 12 g, 0-50% EA/hexanes provided 2-(2-fluoro-4-methylphenyl)-5-(1-phenylcyclobutyl)-thiazolo[5,4-b]pyridine as a light yellow oil that slowly solidified. MS (ESI) m/z: calculated: 374.1; Observed: 375.1 (M++1).

Provenance & Evidence