Methanol → HCID 68635754, compound

Participants

Reaction Conditions

Reaction Steps

1-(3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)ethanone (0.577 g, 2.49 mmol) was added to a solution of (R)-(+)-2-methyl-2-propanesulfinamide (0.150 g, 1.24 mmol), titanium (iv) ethoxide (0.510 mL, 2.48 mmol) in THF (5 mL). The reaction mixture was heated to 70° C. for 23 h, At which time was cooled to −50° C. To the reaction mixture was added a suspension of sodium borohydride (0.187 g, 4.95 mmol) in 0.5 mL of THF also at −50° C., allowed to stir for 18 h at −50° C. The reaction mixture was warmed to 0° C. and MeOH was added dropwise until gas evolution was no longer observed. The crude reaction mixture was poured into an equal volume of brine while being stirred rapidly. The resulting suspension was filtered through a plug of celite, the cake rinsed with EtOAc and MeOH. The filtrate was reduced in vacuo, the residue diluted with EtOAc, extracted with brine and dried over MgSO4. The crude reaction mixture was concentrated in vacuo and purified by silica gel chromatography to afford (R)-N-(1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)ethyl)-2-methylpropane-2-sulfinamide. MS (ESI) m/z: calculated: 493.2; Observed: 494.0 (M++1).

Provenance & Evidence