Boron tribromide → HCID 86613777, compound

Participants

Reaction Conditions

Reaction Steps

To a 25 mL round-bottomed flask was added 6-(2-(2-amino-3-(3-fluoro-4-methoxyphenyl)propylamino)thiazol-5-yl)benzo[d]oxazol-2(3H)-one (Example 129) (60 mg, 145 μmol) and 3 mL of DCM. The solution was cooled to −78° C., and treated dropwise with boron tribromide, 1.0 M in DCM (497 μL, 2895 μmol) via a syringe. The solution was stirred at −78° C. for 1 hour and then allowed to warm to room temperature overnight. The reaction mixture was concentrated, and 2 mL of MeOH was added dropwise. The reaction mixture was purified by preparative LC to give 6-(2-(2-amino-3-(3-fluoro-4-hydroxyphenyl)propylamino)thiazol-5-yl)benzo[d]oxazol-2((H)-one (20 mg, 35% yield). MS m/z: 401 (M+1). 1H NMR (400 MHz, CD3OD) δ ppm 2.85-2.98 (m, 2H), 3.47-3.53 (m, 1H), 3.62-3.71 (m, 2H), 6.92-6.97 (m, 2H), 7.05-7.10 (m, 2H), 7.26 (dd, J=8.02, 1.57 Hz, 1H), 7.37 (s, 1H), 7.38 (d, J=1.37 Hz, 1H).

Provenance & Evidence