Potassium Carbonate → 5-(3-Trifluoromethoxy-phenoxymethyl)-pyrazine-2-carboxylic acid methyl ester

HRID 2373852

Reaction equation

HRID 2373852 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([CH2:11]Br)=[CH:7][N:6]=1)=[O:4].[F:13][C:14]([F:24])([F:23])[O:15][C:16]1[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([CH2:11][O:22][C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([O:15][C:14]([F:13])([F:23])[F:24])[CH:17]=2)=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27332613-(Trifluoromethoxy)phenolHCID 21973569Methyl 5-(bromomethyl)pyrazine-2-carboxylate

Product 1

HCID 692063465-(3-Trifluoromethoxy-phenoxymethyl)-pyrazine-2-carboxylic acid methyl esterYield 88.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-bromomethyl-pyrazine-2-carboxylic acid methyl ester (0.305 g, 1.314 mmol) in DMF (6 mL) was treated with 3-trifluoromethoxyphenol (0.280 g, 1.577 mmol) and potassium carbonate (0.400 g, 2.89 mmol) by the general procedure G. The crude product was purified by flash column chromatography on silica gel to give 0.380 g of pure 5-(3-Trifluoromethoxy-phenoxymethyl)-pyrazine-2-carboxylic acid methyl ester. LCMS: 330 (M+2)+

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-b547a5d1b0354d98b065c0720cf92894
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Linked notes

Loading…