Ammonium Hydroxide → HCID 178452801, compound

HRID 450431Notes

Reaction equation

HRID 450431 reaction equation
[CH3:1][C:2]([O-])=O.[Na+].Br[CH:7](Br)[C:8](=O)[C:9]([F:12])([F:11])[F:10].[C:15]([O:19][C:20](=[O:37])[NH:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:30]=[N:31][C:32](C=O)=[CH:33][CH:34]=2)=[CH:24][CH:23]=1)([CH3:18])([CH3:17])[CH3:16].[OH-].[NH4+:39]>O>[C:15]([O:19][C:20](=[O:37])[NH:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][C:29]2[CH:30]=[CH:2][CH:1]=[C:33]([C:32]3[NH:31][CH:7]=[C:8]([C:9]([F:12])([F:11])[F:10])[N:39]=3)[CH:34]=2)=[CH:26][CH:27]=1)([CH3:16])([CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 517045Sodium AcetateHCID 5505231,1-Dibromo-3,3,3-trifluoroacetoneHCID 86641684HCID 86641684, compound

Product 1

HCID 178452801HCID 178452801, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of NaOAc (0.6 g, 7.4 mmol) in water (1.5 mL) was treated with 3,3-dibromo-1,1,1-trifluoro-propan-2-one (2.2 g, 8.3 mmol) and the resulting mixture was heated to reflux for 30 min. After cooling, the solution was added to [4-(6-formyl-pyridin-3-yloxy)-phenyl]-carbamicacid t-butyl ester (2.3 g, 7.4 mmol) in ammonium hydroxide (30%, 23 mL). The reaction mixture was stirred at RT for 5 h, concentrated in vacuo and purified via chromatography to give {4-[3-(4-trifluoromethyl-1H-imidazol-2-yl)-phenoxy]-phenyl}-carbamic acid t-butyl ester (2.1 g, 67% yield). MS (ESI) m/z: (M+H+) 421.1.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 30 min
  3. temperatureAfter cooling
  4. concentrationconcentrated in vacuo
  5. custompurified via chromatography

Sources & evidence

ORD record
ord-68a2456efdd7495481edde455fe75749
Source dataset
uspto-grants-2013_07
Patent number
US08486951B2

Reaction notes

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