[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]#[N:15])=[CH:12][C:11]([C:16]([F:19])([F:18])[F:17])=[N:10]1.S(C)C.CCOCC.Cl.C(Cl)(Cl)Cl.CO>C1COCC1>[ClH:1].[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([CH2:14][NH2:15])=[CH:12][C:11]([C:16]([F:18])([F:19])[F:17])=[N:10]1To a stirred solution of 1-(2,3-dichlorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonitrile (5.02 g, 16.46 mmol, 1.0 eq.) in THF (50 mL) was added BH3.S(CH3)2 (3.74 g, 49.38 mmol, 3.0 eq.) at 0° C. and heated to reflux for 1 h. The reaction mixture was cooled to 0° C. and quenched with 1N HCl and basified with 1N solution of NaOH to a pH of ˜10 and extracted with ethyl acetate (100 mL×2), dried (Na2SO4), the solvent evaporated to get a pale yellow oil. The oil was treated with ether HCl to get (1-(2,3-dichlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride (1.15, 27% yield over 3 steps) as a white solid (TLC system: CHCl3/MeOH (9:1), Rf 0.55).
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