Methyl iodide → 1-(4-Fluorophenyl)-6-methyl-4-(3-trifluoromethyl-benzylcarbamoyl)-1H-pyrazolo[3,4-c]pyridin-6-ium iodide

HRID 2198093Notes

Reaction equation

HRID 2198093 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][CH:28]=1)[CH2:6][NH:7][C:8]([C:10]1[C:11]2[CH:18]=[N:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[C:12]=2[CH:13]=[N:14][CH:15]=1)=[O:9].[I:31][CH3:32]>C1COCC1>[I-:31].[F:25][C:22]1[CH:23]=[CH:24][C:19]([N:16]2[C:12]3=[CH:13][N+:14]([CH3:32])=[CH:15][C:10]([C:8](=[O:9])[NH:7][CH2:6][C:5]4[CH:26]=[CH:27][CH:28]=[C:3]([C:2]([F:1])([F:29])[F:30])[CH:4]=4)=[C:11]3[CH:18]=[N:17]2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 451380071-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid 3-trifluoromethyl-benzylamide

Product 1

HCID 667272811-(4-Fluorophenyl)-6-methyl-4-(3-trifluoromethyl-benzylcarbamoyl)-1H-pyrazolo[3,4-c]pyridin-6-ium iodide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid 3-trifluoromethyl-benzylamide (0.060 g, 0.14 mmol) in THF (2 mL) was added iodomethane (0.50 mL, 4.0 mmol). The reaction was monitored by TLC (EtOAc-hexanes 4:6). After 11 days, the reaction afforded a white precipitate. The mixture was concentrated under a stream of nitrogen and the residue triturated with ether with a few drops of methanol and then hexanes was added. The solid was collected by filtration to afford the title compound as a yellow solid.

Workup

  1. customthe reaction afforded a white precipitate
  2. concentrationThe mixture was concentrated under a stream of nitrogen
  3. customthe residue triturated with ether with a few drops of methanol
  4. additionhexanes was added
  5. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-449829b932bc4392931eb17f7696d3d1
Source dataset
uspto-grants-2012_12
Patent number
US08338610B2

Reaction notes

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