Dichloromethane → (E)-ethyl 3-(1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)acrylate

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Reaction Conditions

Reaction Steps

To a solution of 3-bromo-1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.026 g, 0.056 mmol, Example #2, Step E) and PdCl2(dppf).DCM (0.005 g, 0.006 mmol) in THF (1 mL) was added (E)-ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate (0.052 g, 0.23 mmol) and Na2CO3 (0.021 g, 0.20 mmol) followed by water (0.25 mL). The mixture was heated to about 65° C. After about 15 h, the mixture was cooled to rt and directly purified by chromatography on silica gel (12 g) eluting with 20 to 80% EtOAc:DCM (1:1) in heptane to provide (E)-ethyl 3-(1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)acrylate (0.045 g, 70%): LC/MS (Table 2, Method a) Rt=3.15 min; MS m/z: 493 (M+H)+.

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