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, 3 g, 11.8 mmol, 1.0 equiv), potassium vinyltrifluoroborate (31-1, 3.2 g, 23.7 mmol, 2.0 equiv), Cs2CO3 (11.6 g, 35.5 mmol, 3.0 equiv) and 1,1′-bis(diphenylphosphino)-ferrocene-palladium(II)dichloride dichloromethane complex (0.97 g, 1.2 mmol, 0.10 equiv) were added to 1,4-dioxane (19.7 mL) and water (3.9 mL). The resulting reaction mixture was heated to 100° C. and stirred for 18 h. Following this duration, LCMS showed complete 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 brown semi-solid. Purification by normal-phase HPLC (0-40% EtOAc:hexane) afforded 31-2 as a yellow solid. MS m/z (M+H): calculated=246.1601; observed=246.1608.

1. customThe resulting reaction mixture
2. customconsumption of 1-4
3. filtrationThe contents were filtered through Celite
4. washwashed with ethyl acetate (10 mL)
5. additionThe filtrate was diluted with saturated NaHCO3 (50 mL)
6. customthe layers were separated
7. extractionThe aqueous layer was back-extracted with ethyl acetate (3×20 mL)
8. dry with materialthe combined organics were dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customto give a brown semi-solid
12. customPurification by normal-phase HPLC (0-40% EtOAc:hexane)