Dimethylacetamide → 6-Chloro-1H-indazole-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A DMA (48 mL) solution containing the intermediate from Step B (4.0 g, 14.36 mmol), zinc powder (113 mg, 1.72 mmol), zinc cyanide (1.01 g, 8.86 mmol), 1,1′-bis(diphenylphosphino)ferrocene (318 mg, 0.58 mmol) and tris(dibenzylideneacetone)dipalladium (263 mg, 0.29 mmol) was heated at 120° C. for 45 minutes. The solution was cooled to room temperature and partitioned between EtOAc and 0.5M HCl aq. The organic phase was washed twice with 0.5M HCl aq and brine. The organic phase was then dried over MgSO4, filtered and concentrated. The crude material was purified by silica gel chromatography using a hexanes/EtOAc gradient to give the indicated product. 1H NMR (400 MHz, CH3 CN-d3): δ 7.83 (d, J=8.7 Hz, 1H); 7.77 (d, J=1.7 Hz, 1H); 7.36 (dd, J=8.7, 1.7 Hz, 1H). m/z=178.1 (M+H).

Provenance & Evidence