Dichloromethane → HCID 58381987, compound

Participants

Reaction Steps

1-Cyclohexyl-6-((2-(trimethylsilyl)ethoxy)methyl)-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (0.100 g, 0.259 mmol), 4-(methylsulfonyl)phenylboronic acid (0.103 g, 0.517 mmol, Acros), TEA (0.072 mL, 0.52 mmol) and 4 Å molecular sieves (130 mg) were added to DCM (2.6 mL) in a vial. Copper (II) acetate (0.047 g, 0.259 mmol) (Aldrich) was added in one portion and the vial was sealed. The mixture was stirred for about 22 h at rt. DCM (15 mL), water (5 mL), and concentrated NH4OH (5 mL) were added and the layers separated. The aqueous layer was extracted with DCM (5 mL). The combined organic layers were washed with water (10 mL), washed with brine (10 mL), dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (25 g Silicycle™ column) eluting with 10-50% EtOAc in DCM to give 1-cyclohexyl-3-(4-(methylsulfonyl)phenyl)-6-((2-(trimethylsilyl)ethoxy)methyl)-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (0.068 g, 48%): LCMS (Table 2, Method b) Rt=3.16 min.; MS m/z: 541 (M+H)+.

Provenance & Evidence