Water → 5-[(1E)-4-{[tert-Butyl(dimethyl)silyl]oxy}but-1-en-1-yl]-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence