Hydrochloric Acid → 6-(2,6-dichloro-3,5-dimethoxyphenyl)-1H-pyrazolo[4,3-c]pyridine

HRID 1778692Notes

Reaction equation

HRID 1778692 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[N:18]=[CH:17][C:16]2[CH:19]=[N:20][N:21](C3CCCCO3)[C:15]=2[CH:14]=1.Cl.C(Cl)(=O)C>CO>[Cl:12][C:4]1[C:5]([O:10][CH3:11])=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Cl:1])[C:3]=1[C:13]1[N:18]=[CH:17][C:16]2[CH:19]=[N:20][NH:21][C:15]=2[CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 867228196-(2,6-dichloro-3,5-dimethoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 867228206-(2,6-dichloro-3,5-dimethoxyphenyl)-1H-pyrazolo[4,3-c]pyridineYield 100.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

At 0° C. (with ice-bath) to a stirring solution of 6-(2,6-dichloro-3,5-dimethoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine (0.78 g, 1.9 mmol) in methanol (10 mL) was added drop-wise a pre-cooled (with ice-bath) HCl solution prepared from acetyl chloride (2.72 mL, 38.2 mmol) in methanol (15 mL). After the addition, the ice-bath was removed. The mixture was stirred at r.t. for 2 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 (0.62 g). LC/MS (M+H)+=324.0.

Workup

  1. additionAfter the addition
  2. customthe ice-bath was removed
  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-b588c5fe31294b60aadb5055b310f0cc
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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