Methyl bromoacetate → {4-[2-(2,4-Dichloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-pyridin-2-yloxy}-acetic acid methyl ester

HRID 1097876Notes

Reaction equation

HRID 1097876 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:23])[C:10]([C:16]1[CH:21]=[CH:20][NH:19][C:18](=[O:22])[CH:17]=1)([OH:15])[C:11]([F:14])([F:13])[F:12].[CH3:24][O:25][C:26](=[O:29])[CH2:27]Br>C1(C)C=CC=CC=1>[CH3:24][O:25][C:26](=[O:29])[CH2:27][O:22][C:18]1[CH:17]=[C:16]([C:10]([OH:15])([C:11]([F:14])([F:13])[F:12])[CH:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[CH3:23])[CH:21]=[CH:20][N:19]=1

Participants

4

Reactant 2

HCID 60984Methyl bromoacetateHCID 57421256HCID 57421256, compound

Product 1

HCID 25254606{4-[2-(2,4-Dichloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-pyridin-2-yloxy}-acetic acid methyl esterYield 45.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
145 °C

Procedure

To a solution of 4-[2-(2,4-dichloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1H-pyridin-2-one (100 mg) in toluene (5 mL) was added bromoacetic acid methyl ester (50 mg, 0.03 mL) and Ag2CO3 (53 mg) and the mixture was allowed to stir for 3.5 hours at 145° C. The mixture was cooled to room temperature, filtered and the residue was purified by flash chromatography (10 silica gel cartridge, using ethyl acetate/heptane 1:9 as an eluent) to provide the title compound as a colorless oil (54 mg). MS (m/e): 438.1 (MH+).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. customthe residue was purified by flash chromatography (10 silica gel cartridge

Sources & evidence

ORD record
ord-3b654bd97079420098aaa7adeb161a4d
Source dataset
uspto-grants-2012_03
Patent number
US08143280B2

Reaction notes

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