Dimethylformamide → HCID 73336116, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(4-chloro-5-methyl-3-iodopyrazol-1-yl)-1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]ethanone (430 mg, 0.86 mmol), Zn(CN)2 (151 mg, 1.3 mmol), dppf (72 mg, 0.14 mmol), and Pd2(dba)3 (79 mg, 0.09 mmol) in DMF (10 mL) and water (0.5 mL) was heated at 90° C. overnight. After cooling to room temperature, the reaction mixture was diluted with EtOAc (30 mL) and washed with water (3×5 mL). The EtOAc layer was dried (Na2SO4), filtered, and concentrated in vacuo. The residue was triturated with 1:1 CH2Cl2/MeOH (3×5 mL) to give the desired product as white powder (250 mg, 72%). 1H NMR (400 MHz, DMSO-d6) δ 8.15 (s, 1H), 7.58 (m, 2H), 7.35 (dd, J=8.7, 8.1 Hz, 2H), 5.58 (s, 2H), 3.80 (m, 2H), 2.84 (t, J=5.4 Hz, 2H), 2.25 (s, 3H), 2.00 (m, 2H); MS: (ES) m/z calculated for C19H17ClF4N5O [M+H]+ 399.1, found 399.1.

Provenance & Evidence