1,1'-Carbonyldiimidazole → 5-((6-Bromobenzo[d]thiazol-2-yl)methyl)-1,3,4-oxadiazol-2-ol

Participants

Reaction Steps

To a suspension of 2-(6-bromobenzo[d]thiazol-2-yl)acetohydrazide (500 mg, 1.75 mmol) (described in WO 2011/074560) in 1,2-dichloroethane (15 mL) at 0° C. was added CDI (340 mg, 2.10 mmol) then the reaction mixture allowed to warm to room temperature and stirred for 2 h. The reaction mixture was concentrated under reduced pressure and the residue purified on silica gel chromatography eluting with 0 to 10% MeOH/DCM to give Compound 51a (296 mg, 54% yield) as a white solid. LCMS=0.84 min using analytical method (M), 502.0 (M+H). 1H NMR (400 MHz, CDCl3 containing CD3OD) δ 8.02 (d, J=1.8 Hz, 1H), 7.84 (d, J=8.5 Hz, 1H), 7.59 (dd, J=8.7, 1.9 Hz, 1H), 4.38 (s, 2H).

Provenance & Evidence