Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → 2-(4-(Benzyloxy)-3,5-dimethylphenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(benzyloxy)-3,5-dimethylbenzoic acid (238.0 mg, 929 μmol) and thionyl chloride (2.5 mL, 34.25 mmol) was heated at 70° C. for 1 h and then concentrated in vacuo. 3-Amino-6-(1-phenylcyclopropyl)pyridine-2(1H)-thione (225 mg, 0.929 mmol) was added to the residue, and the resulting mixture was and heated in toluene (9.0 mL) at 100° C. for 10 min. (±)-10-Camphorsulfonic acid (194 mg, 836 μmol) was subsequently added, and the resulting mixture was heated at 100° C. for 30 min. The reaction solution was then cooled to 25° C. and concentrated onto silica gel. Chromatographic purification (silica gel, 0-40% ethyl ether/hexanes) provided 2-(4-(benzyloxy)-3,5-dimethylphenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine as a white solid. MS (ESI) m/z: Calculated: 462.2; Observed: 463.2 (M++1).

Provenance & Evidence