S(Cl)([Cl:3])=O.[C:5]1([N:11]2[C:19]3[CH2:18][CH2:17][CH2:16][CH:15]([CH2:20][CH2:21]O)[C:14]=3[CH:13]=[N:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:3][CH2:21][CH2:20][CH:15]1[CH2:16][CH2:17][CH2:18][C:19]2[N:11]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:12]=[CH:13][C:14]1=2Thionyl cloride (4 mL) is slowly added at room temperature over a solution of 2-(4,5,6,7-tetrahydro-1-phenyl-1H-indazol-4-yl)ethanol (516 mg, 2.13 mmol) in 25 mL of toluene. The reaction mixture is heated at 90° C. during 2 hours. The solvent is eliminated at reduced pressure. The crude is diluted in ethyl acetate and washed twice with a NaHCO3 solution. The solvent is next evaporated at reduced pressure, to obtain 4-(2-chloroethyl)-4,5,6,7-tetrahydro-1-phenyl-1H-indazole (423 mg, 1.62 mmol, 76%, oil).
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