[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[CH:4][C:3]=1[C:12]1[N:17]=[CH:16][C:15]2[C:18]([I:27])=[N:19][N:20]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][O:22]3)[C:14]=2[CH:13]=1.S(Cl)([Cl:31])(=O)=O>C(Cl)Cl>[Cl:31][C:4]1[C:5]([O:10][CH3:11])=[CH:6][C:7]([O:8][CH3:9])=[C:2]([F:1])[C:3]=1[C:12]1[N:17]=[CH:16][C:15]2[C:18]([I:27])=[N:19][N:20]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][O:22]3)[C:14]=2[CH:13]=1At r.t. to a solution of 6-(2-fluoro-3,5-dimethoxyphenyl)-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine (35 mg, 0.072 mmol) (Example 52, Step 4) in methylene chloride (3 mL) was added sulfuryl chloride (7.0 μL, 0.087 mmol). The mixture was stirred at r.t. for 20 min then concentrated. The solid was filtered out and the crude material was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (0.025 g). LCMS (M+H)+=518.1.
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