Dichloromethane → HCID 24983902, compound

Participants

Reaction Steps

4-(2-oxo-3-(2-(Tetrahydro-2H-pyran-4-yl)ethyl)-2,3-dihydro-1H-imidazol-[4,5-b]pyrazin-5-yl)benzamide. 6-Bromo-1-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one (0.400 g, 1.22 mmol), 4-carboxamide-phenylboronic acid (0.241 g, 1.46 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (0.098 g, 0.12 mmol), potassium phosphate (1.03 g, 4.88 mmol), water (2 ml) and dimethylformamide (7 mL) were reacted according to General Procedure B. The solution was condensed under reduced pressure and the product was crystallized from dichloromethane to give (0.400 g, 89% yield). 1H NMR (400 MHz, CD3OD) δ 8.54 (s, 1H) 8.40 (s, 1H), 8.09 (d, J=8.4, 2H), 7.94 (d, J=8.4, 1H), 4.08 (t, J=6.8, 2H), 3.92 (dd, J=11.2, 3.2, 2H), 3.64 (m, 2H), 1.83 (m, 4H), 1.59 (m, 1H), 1.38 (qd, J=12.8, 4.4, 2H); MS (ESI) m/z 368.4 [M+1]+; mp 233-236° C.

Provenance & Evidence