反应详情

To a stirred solution of 3-(2-fluoro-4-trifluoromethyl-phenyl)-5-(4-methoxy-phenyl)-3H-[1,2,3]triazol-4-ylamine (14) (0.400 g, 1.1354 mmol) in anhydrous dichloromethane (25 ml), cooled to −78° C. and under a nitrogen flow, a solution of boron tribromide (1.991 g, ˜0.75 ml, 7.9478 mmol) in 5 ml of anhydrous dichloromethane is added drop-wise. The mixture is allowed to reach room temperature spontaneously overnight and it is then cooled again in an ice-salt bath and the excess of the reagent is decomposed upon drop-wise addition of 10 ml of methanol and 10 ml of water. After 5 min stirring, 10% sodium hydroxide solution (10 ml) is added and the aqueous layer, once separated, is acidified with 10% hydrochloric acid solution and extracted with chloroform (3×70 ml). The combined organic layers are dried over MgSO4, filtered and evaporated to afford a solid residue (0.350 g). This is purified by column chromatography over silica gel (60-120 mesh) eluting with 16% ethyl acetate in hexane (0.150 g, 40% yield). M.p. 163.5-165.2° C. LC-ESI-HRMS of [M+H]+ shows 339.0853 Da. Calc. 339.086898 Da, dev. −4.7 ppm.

1. temperatureit is then cooled again in an ice-salt bath
2. customthe aqueous layer, once separated
3. extractionextracted with chloroform (3×70 ml)
4. dry with materialThe combined organic layers are dried over MgSO4
5. filtrationfiltered
6. customevaporated