反应详情

温度

100 °C

5-Chloro-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1-4, 1.0 g, 3.9 mmol, 1.0 equiv), tert-butyl(dimethyl){[(3E)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl]oxy}silane (32-1, 2.1 mL, 5.9 mmol, 1.5 equiv), Cs2CO3 (2.6 g, 7.9 mmol, 2.0 equiv) and Bis(tri-tert-butylphosphine)palladium(0) (0.40 g, 0.79 mmol, 0.2 equiv) were added to water (0.94 mL) and 1,4-dioxane (4.7 mL). The resulting mixture was heated to 100° C. and stirred for 18 h. Following this duration, LCMS showed consumption of 1-4. The contents were filtered through Celite and washed with ethyl acetate (10 mL). The filtrate was diluted with saturated NaHCO3 (50 mL) and the layers were separated. The aqueous layer was back-extracted with ethyl acetate (3×20 mL) and the combined organics were dried over Na2SO4, filtered and concentrated in vacuo to give a dark red oil. Purification by normal-phase HPLC (0-30% EtOAc:hexane) afforded 32-2 as an orange oil. MS m/z (M+H): calculated=404.2728; observed=404.2736.

1. customconsumption of 1-4
2. filtrationThe contents were filtered through Celite
3. washwashed with ethyl acetate (10 mL)
4. additionThe filtrate was diluted with saturated NaHCO3 (50 mL)
5. customthe layers were separated
6. extractionThe aqueous layer was back-extracted with ethyl acetate (3×20 mL)
7. dry with materialthe combined organics were dried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto give a dark red oil
11. customPurification by normal-phase HPLC (0-30% EtOAc:hexane)