Thionyl Chloride → HCID 67111742, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3,3-difluorocyclobutanecarboxylic acid (542.6 mg, 3.99 mmol) in thionyl chloride (5.24 mL, 71.8 mmol) was heated at 70° C. for 1 h and then concentrated in vacuo. 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(trimethylstannyl)thiazolo[5,4-b]pyridine (1.08 g, 2.254 mmol) was added to the residue, and the mixture was taken up in toluene (20.0 mL) and stirred under argon at 80° C. for 16 h. The reaction mixture was then concentrated onto silica gel and chromatographically purified (0-60% EtOAc/hexanes) to provide (2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)thiazolo[5,4-b]pyridin-5-yl)(3,3-difluorocyclobutyl)methanone as an off-white solid. MS (ESI) m/z: Calculated: 434.1; Observed: 435.0 (M++1).

Provenance & Evidence