反应详情

温度

110 °C

3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (69 mg, 0.296 mmol), the product of Step 2 (104 mg, 0.296 mmol), X-Phos (14.11 mg, 0.030 mmol), cesium carbonate (289 mg, 0.888 mmol), and Pd2(dba)3 (13.55 mg, 0.015 mmol) were placed in a flask flushed with Ar. Degassed Dioxane (1.2 ml) and Water (0.12 ml) were added and heated to 110° C. for 5.5 h. The reaction was allowed to cool to room temperature and then quenched with saturated aqueous sodium bicarbonate and extracted with EtOAc (3×). The combined organics were dried over Na2SO4, filtered and concentrated in vacuo. Purification via silica gel column chromatography (10-30% EtOAc:hexanes) afforded 2-[5-(3-amino-5-methylphenyl)-1,3-thiazol-2-yl]-1-{[tert-butyl(dimethyl)silyl]oxy}propan-2-ol (82 mg, 73%) as a brown oil. MS ESI: [M+H]+ m/z 379.

1. customflushed with Ar
2. additionDegassed Dioxane (1.2 ml) and Water (0.12 ml) were added
3. temperatureto cool to room temperature
4. customquenched with saturated aqueous sodium bicarbonate
5. extractionextracted with EtOAc (3×)
6. dry with materialThe combined organics were dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customPurification via silica gel column chromatography (10-30% EtOAc:hexanes)