Water → HCID 86727152, compound

HRID 579330Notes

Reaction equation

HRID 579330 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])=[N:9]2)=[CH:4][C:3]=1[O:20][CH3:21].[C:22]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([N:13]([CH3:22])[C:14](=[O:19])[C:15]([F:18])([F:16])[F:17])=[N:9]2)=[CH:4][C:3]=1[O:20][CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86727151HCID 86727151, compound

Product 1

HCID 86727152HCID 86727152, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of N-(1-(4-bromo-3-methoxyphenyl)-1H-pyrazol-3-yl)-2,2,2-trifluoroacetamide (320 mg, 0.879 mmol) and K2CO3 (146 mg, 1.055 mmol) in DMF (2 mL) was added MeI (202 mg, 1.055 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into water and extracted with Et2O. The combined organic layers were washed with water, dried over Na2SO4, filtered and concentrated under reduced pressure to give N-(1-(4-bromo-3-methoxyphenyl)-1H-pyrazol-3-yl)-2,2,2-trifluoro-N-methylacetamide (300 mg, MS: 380.0 [M+H+]).

Workup

  1. extractionextracted with Et2O
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9d2056afe9f947acbfec12723a848a1e
Source dataset
uspto-grants-2015_05
Patent number
US09040712B2

Reaction notes

Loading…