Potassium Carbonate → 6-chloro-4-methyl-3-(trifluoromethoxy)-1-trityl-1H-pyrazolo[4,3-c]pyridine

HRID 588105Notes

Reaction equation

HRID 588105 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]2[C:9](=[O:31])[NH:10][N:11]([C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:38][C:39]([F:50])([F:49])I1C2C=CC=CC=2CO1>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]2[C:9]([O:31][C:39]([F:50])([F:49])[F:38])=[N:10][N:11]([C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1182721366-chloro-4-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridin-3(2H)-one2×HCID 1317344281-Trifluoromethyl-1,2-benziodoxol

Product 1

HCID 1182718936-chloro-4-methyl-3-(trifluoromethoxy)-1-trityl-1H-pyrazolo[4,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-chloro-4-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridin-3(2H)-one (Intermediate 4B, 207.1 mg, 0.486 mmol), potassium carbonate (217.6 mg, 1.574 mmol) and 1-trifluoromethyl-1,2-benziodoxol-3-(1H-one (227.3 mg, 0.719 mmol) in DMF (2 ml) was stirred at RT for 16.5 hr, then heated to 60° C. for 5 hr. Added water and filtered to collect precipitate, which was purified via flash chromatography (0-100% EtOAc/Hex) to provide 6-chloro-4-methyl-3-(trifluoromethoxy)-1-trityl-1H-pyrazolo[4,3-c]pyridine. MS: [M+H]+ m/z 494.

Workup

  1. temperatureheated to 60° C. for 5 hr
  2. filtrationAdded water and filtered
  3. customto collect precipitate, which
  4. customwas purified via flash chromatography (0-100% EtOAc/Hex)

Sources & evidence

ORD record
ord-06c21084fa3a45088c078c023ddc3d2e
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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