反应详情

温度

90 °C

1-{5-[7-Bromo-2-(3-ethyl-ureido)-benzothiazol-5-yl]-pyrimidin-2-yl}-4-methyl-piperidine-4-carboxylic acid ethyl ester (50 mg), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (28 mg), PdCl2(dppf).DCM (4 mg), potassium fluoride (16 mg), 1,4-dioxane (1.5 mL) and water (0.5 mL) were combined in a 0.5-2 mL microwave vial, degassed and heated in a pre-heated oil bath at 90° C. overnight. The mixture was cooled to rt, diluted with water and extracted into EtOAc (4×10 mL). The organic phase was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by Biotage Si chromatography, 12 g Grace cartridge, 4-5% MeOH in DCM. The relevant fractions were combined to give a solid (56 mg) which was purified again by Biotage Si chromatography, 12 g Grace cartridge, 2% MeOH in DCM isocratic. The relevant fractions were combined to give the desired product as a light orange solid (27 mg, 60%). m/z: 495 [M+H]+.

1. customdegassed
2. temperatureThe mixture was cooled to rt
3. additiondiluted with water
4. extractionextracted into EtOAc (4×10 mL)
5. washThe organic phase was washed with brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated in vacuo
8. customThe residue was purified by Biotage Si chromatography, 12 g Grace cartridge, 4-5% MeOH in DCM