Dichloromethane → HCID 53237067, compound

Participants

Reaction Conditions

Reaction Steps

To the solution of 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (116 mg, 0.44 mmol), 7-bromo-1-methylfuro[3,4-c]pyridin-3(1H)-one (100 mg, 0.44 mmol) and PdCl2(dppf).CH2Cl2 (28.6 mg, 0.035 mmol) in DMF (5 mL) was added a solution of Na2CO3 (0.44 mL, 2M) under Nitrogen atmosphere. The mixture was stirred and heated at 100° C. for 4 hrs. The mixture was warmed up room temperature, and solvent was removed in vacuo. The residue was dissolved in DCM and saturated NH4Cl solution. After extraction with DCM and separation, the combined extracts were dried over Na2SO4, filtered and concentrated. The residue was purified by ISCO 40 g (10% MeOH/DCM, v/v, 0-25%) to give 19 mg of the titled compound. ESI-MS m/z: 284.9 [M+1]+, Retention time 1.32 min; 1H-NMR (MeOD, 400 MHz) δ 1.31 (d, J=6.8 Hz, 3H), 6.23 (q, J=6.8 Hz, 1H), 7.79 (dd, J=8.0, 1.6 Hz, 1H), 8.01 (d, J=1.6 Hz, 1H), 8.04 (d, J=8.0 Hz, 1H), 8.94 (s, 1H), 9.17 (s, 1H).

Provenance & Evidence