Dimethylformamide → HCID 18801617, compound

HRID 1422834Notes

Reaction equation

HRID 1422834 reaction equation
CN(C)C=O.[CH3:6][O:7][C:8](=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=1.CC(C)([O-])C.[K+].Br[C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][N:25]=1>O>[CH3:6][O:7][C:8](=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][N:25]=2)[CH:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 88068Methyl 3-HydroxybenzoateHCID 27364342-Bromo-5-(trifluoromethyl)pyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 18801617HCID 18801617, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dimethylformamide (1.0 mL) solution of 3-hydroxy-benzoic acid methyl ester (183 mg, 1.2 mmol) was added potassium t-butoxide (147 mg, 1.2 mmol). Upon stirring the reaction at room temperature for 15 min, 2-bromo-5-trifluoromethyl-pyridine (300 mg, 1.32 mmol) was added. The reaction was stirred at room temperature for 15 h. Crude reaction mass was added to water, aqueous layer was acidified to pH 4.0 and product was extracted with ethyl acetate to give 3-(5-trifluoromethyl-pyridin-2-yloxy)-benzoic acid methyl ester (285 mg).

Workup

  1. customthe reaction at room temperature for 15 min
  2. stirringThe reaction was stirred at room temperature for 15 h
  3. customCrude reaction mass
  4. extractionwas extracted with ethyl acetate

Sources & evidence

ORD record
ord-9ee079b8cce74ebeba854fb91f16b41d
Source dataset
uspto-grants-2015_01
Patent number
US08927549B2

Reaction notes

Loading…