Methyl iodide → 6-chloro-3-methoxy-4-(trifluoromethyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine

HRID 588104Notes

Reaction equation

HRID 588104 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]2[C:12](=[O:15])[NH:13][NH:14][C:4]=2[CH:3]=1.[C:16](Cl)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[H-].[Na+].[C:38](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([F:10])([F:11])[F:9])[C:5]2[C:12]([O:15][CH3:38])=[N:13][N:14]([C:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:4]=2[CH:3]=1

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 6456Trityl chlorideHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 1182724906-chloro-4-(trifluoromethyl)-1H-pyrazolo[4,3-c]pyridin-3(2H)-one

Product 1

HCID 1182720386-chloro-3-methoxy-4-(trifluoromethyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-chloro-4-(trifluoromethyl)-1H-pyrazolo[4,3-c]pyridin-3(2H)-one (290 mg, 1.221 mmol) in DMF (5 ml) was charged with trityl chloride (369 mg, 1.324 mmol) followed by sodium hydride (58 mg, 1.450 mmol). Stirred at RT for 2.5 hr. Added potassium carbonate (0.53 g, 3.83 mmol) and methyl iodide (0.20 ml, 3.20 mmol) then stirred at RT for 3 hr. Quenched with water and filtered to remove ppt, which was dried under vacuum to provide crude 6-chloro-3-methoxy-4-(trifluoromethyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine, used as-is. MS: [M+H]+ m/z 494.

Workup

  1. customQuenched with water
  2. filtrationfiltered
  3. customto remove ppt, which
  4. customwas dried under vacuum

Sources & evidence

ORD record
ord-60cffc016dfe425f85a7f7e294625599
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

Loading…