Water → HCID 86727153, compound

HRID 579331Notes

Reaction equation

HRID 579331 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([N:13](C)[C:14](=O)C(F)(F)F)=[N:9]2)=[CH:4][C:3]=1[O:21][CH3:22].[O-]CC.[Na+].O>CCO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([NH:13][CH3:14])=[N:9]2)=[CH:4][C:3]=1[O:21][CH3:22]

Participants

5

Reactant 3

HCID 962WaterHCID 2723922Sodium ethoxideHCID 86727152HCID 86727152, compound

Product 1

HCID 86727153HCID 86727153, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To an ice cold solution of N-(1-(4-bromo-3-methoxyphenyl)-1H-pyrazol-3-yl)-2,2,2-trifluoro-N-methylacetamide (300 mg, 0.793 mmol) in EtOH (5 mL) was added a solution of 21% sodium ethoxide in EtOH (0.4 mL, 0.793 mmol). The mixture was stirred at room temperature overnight, then was poured into water. The mixture was extracted with EtOAc. The combined organic layers were washed with aqueous saturated NaHCO3 solution, dried over Na2SO4, filtered and concentrated under reduced pressure to give 1-(4-bromo-3-methoxyphenyl)-N-methyl-1H-pyrazol-3-amine (200 mg, MS: 284.3 [M+H+]).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washThe combined organic layers were washed with aqueous saturated NaHCO3 solution
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e97a49b40393407bb62a44bde5445e8a
Source dataset
uspto-grants-2015_05
Patent number
US09040712B2

Reaction notes

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