Boron tribromide → HCID 135723770, compound

Participants

Reaction Steps

To a stirred solution of the product from Example 18.2 (0.056 g, 0.14 mmol) in DCM (7 ml) at −78° C. was added boron tribromide (1.39 ml, 1.39 mmol, 1.0M in DCM). After 15 mins the reaction mixture was warmed to ambient temperature and coevaporated with methanol (3×). The residue was stirred in methanol (7N ammonia solution) for 10 mins and evaporated on to silica gel. The material was chromatographed on silica gel (chloroform-methanol-conc. ammonia, 10:9:1) giving a white solid (17 mg, 46%). 1H NMR (D2O) δ 8.03 (s, 1H), 7.59 (s, 1H), 4.41 (ABq, 2H), 3.88 (dd, J=13.2, 4.2 Hz, 1H), 3.80 (m, 1H), 3.72 (dd, J=13.2, 5.3 Hz, 1H), 3.60 (dd, J=12.5, 3.4 Hz, 2H), 3.47 (dd, J=12.5, 4.5 Hz, 1H), 3.26 (m, 1H). +ESMS found 269.1262 (M+H)+ C11H17N4O4 requires 269.1250.

Provenance & Evidence