Dichloromethane → 6-(2,6-dichloro-3,5-dimethoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine

HRID 1778691Notes

Reaction equation

HRID 1778691 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[CH:15][C:14]3[CH:17]=[N:18][N:19]([CH:20]4[CH2:25][CH2:24][CH2:23][CH2:22][O:21]4)[C:13]=3[CH:12]=2)C=[C:7]([O:9][CH3:10])[CH:8]=1.S(Cl)([Cl:29])(=O)=O.[CH2:31]([Cl:33])Cl>>[Cl:29][C:4]1[C:3]([O:2][CH3:1])=[CH:8][C:7]([O:9][CH3:10])=[C:31]([Cl:33])[C:5]=1[C:11]1[N:16]=[CH:15][C:14]2[CH:17]=[N:18][N:19]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][O:21]3)[C:13]=2[CH:12]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24648Sulfuryl chloride2×HCID 867228186-(3,5-dimethoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 867228196-(2,6-dichloro-3,5-dimethoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine

Procedure

At r.t. to a solution of 6-(3,5-dimethoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine (0.66 g, 1.9 mmol) in methylene chloride (10 mL) with stirring was added drop-wise sulfuryl chloride (300 μL, 3.7 mmol)(Acros Organics, Cat. No. 37815). The mixture was stirred at r.t. for 2 h. LCMS showed 25% product formed, and 75% was mono-chlorinated product. Additional sulfuryl chloride (100 μL) was added to the mixture. It was stirred at r.t. for 5 h, and then concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (0.78 g). LCMS (M+H)+=408.0.

Workup

  1. customformed
  2. stirringIt was stirred at r.t. for 5 h
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%)

Sources & evidence

ORD record
ord-18d7f23823024687b0f1696ce69a5fe2
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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