Sodium Carbonate → HCID 178516213, compound

Participants

Reaction Steps

6-(4-(1H-1,2,4-Triazol-3-yl)phenyl)-1-(2-(2-oxopyrrolidin-1-yl)ethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one 6-Bromo-1-(2-(2-oxopyrrolidin-1-yl)ethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one (See Example 157.A) (290 mg, 0.8 mmol), 4-(1H-1,2,4-triazol-5-yl)phenylboronic acid hydrochloride (See Example 159.D) (224 mg, 0.99 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (30 mg, 0.04 mmol), 1M sodium carbonate (2.5 mL, 2.5 mmol), and dioxane (5 mL) were heated in a Biotage Emrys Optimizer microwave reactor at 150° C. for 1 h. The reaction was purified by reverse-phase semi-preparatory HPLC (10-70% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min). The product fractions were passed through a Strata-XC ion-exchange column and the product was released from the column with 2M ammonia in methanol. The solution was concentrated and the resulting material was triturated with either to give a white solid (23 mg, 7% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.58 (s, 1H), 8.48 (br, 1H), 8.20 (d, J=10.0, 2H), 8.13 (d, J=10.0, 2H), 4.06 (m, 2H), 3.58 (m, 2H), 3.52 (t, J=6.8, 2H), 1.85 (d, J=7.8, 2H), 1.74 (m, 2H); MS (ESI) m/z 391.5 [M+1]+; mp 300-301° C.

Provenance & Evidence