Boron tribromide → 4-{2-[4-(2-Pyrrolidin-1-yl-ethoxy)-phenylamino]-thiazol-5-yl}-phenol

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Reaction Steps

A 1 N solution of BBr3 in CH2Cl2 (0.4 mL, 0.404 mmol, 8.0 equiv) is added dropwise to a cold (−10° C.) solution of [5-(4-methoxy-phenyl)thiazol-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine (Example 3) (20 mg, 0.0506 mmol) in CH2Cl2 (0.4 mL), under an argon atmosphere. The reaction mixture is allowed to warm to RT and to stir for 1.5 h. The mixture is then cooled to 0° C. and quenched with MeOH. The resulting red solution is concentrated in vacuo. Purification of the crude material by silica gel (9 g) column chromatography (CH2Cl2/MeOH, 90/10) affords the title compound as a beige solid: ES-MS: 382.0 [M+H]+; single peak at tR=5.47 min (System 1); Rf=0.28 (CH2Cl2/MeOH, 80/20).

Provenance & Evidence