Dimethylformamide → HCID 11339645, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(2-bromophenyl)-3-(4-chlorophenyl)-7-(2,2-difluoropropoxy)-5-methyl-2H-pyrazolo[4,3-d]pyrimidine (10A-7, 50 mg, 0.1 mmol), Zn(CN)2(20 mg, 0.17 mmol), Pd(PPh3)4 (15 mg, 0.01 mmol) in DMF (1 ml) was heated in a microwave apparatus (Emrys Optimizer, Personal Chemistry) at 200° C. for 3 minutes. The reaction mixture was quenched with saturated aqueous NaCl and extracted with ethyl acetate (2×). The combined organic extracts were dried and concentrated under vacuum. The crude residue was purified via HPLC (Shimadzu) using a solvent gradient of 30% CH3CN/hexanes to 100% CH3CN to give the desired product, 2-[3-(4-chlorophenyl)-7-(2,2-difluoropropoxy)-5-methylpyrazolo[4,3-d]pyrimidin-2-yl]-benzonitrile (11A-1), as a colorless solid (25 mg): MS (M+1)+440.0; 1H NMR (400 MHz, CDCl3) δ 7.80-7.64 (m, 4H), 7.40-7.26 (m, 4H), 4.8 (t, J=11.6 Hz, 2H), 2.7 (s, 3H), 1.79 (t, J=18.67 Hz, 3H).

Provenance & Evidence