Tetrahydrofuran → HCID 67112059, compound

Participants

Reaction Conditions

Reaction Steps

To 1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)ethanone (0.732 g, 1.88 mmol) in diethyl ether (15.7 mL) and toluene (14.7 mL) at 0° C. under argon was added methylmagnesium chloride, 3.0 M solution in THF (1.38 mL, 4.14 mmol). After stirring at 0° C. for 10 minutes, the reaction mixture was allowed to warm to room temperature and stirred for another 1 hour. The reaction mixture was quenched with saturated NH4Cl solution and diluted with CH2Cl2; the aqueous layer was back-extracted with CH2Cl2. The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. ISCO purification with 10% to 30% EtOAc/Hexanes afforded 2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)propan-2-ol as a colorless foam. MS (ESI) m/z: Calculated: 404.1; Observed: 405.1 (M++1).

Provenance & Evidence