Ammonia → HCID 66774989, compound

Participants

Reaction Conditions

Reaction Steps

A 250 ml round-bottomed flask is charged with 4 g of a mixture of the regioisomers of 7-cyano-5-(2,6-difluorophenyl)pyrazolo[4,3-c]isoquinoline-1-sulphonic acid dimethylamide in 160 ml of DCM. After cooling to 0° C. using an ice bath, 108 ml of TFA are added and the mixture is stirred at RT for 6 h. The mixture is concentrated under RP and the solid obtained is taken up in 600 ml of water, and 50 ml of 0.75 M ammonia solution are added. The aqueous phase is extracted with 3 times 150 ml of AcOEt. The organic extracts are combined, washed with saturated NaCl solution and then dried over MgSO4. Concentration of the AcOEt under RP gives 2.6 g of 5-(2,6-difluorophenyl)-1H-pyrazolo[4,3-c]isoquinoline-7-carbonitrile (beige solid). MS (E/I): m/z=306 (M+); 1H NMR: 7.38 (t, J=8.0 Hz, 2H); 7.72 (m, 1H); 8.24 (broad s, 1H); 8.34 (dd, J=1.5 and 8.5 Hz, 1H); 8.59 (s, 1H); 8.70 (d, J=8.5 Hz, 1H); 14.5 (very broad m, 1H).

Provenance & Evidence