Methyl iodide → Methyl 2-(4-(3-chloropyrazin-2-yl)phenyl)acetate

HRID 474143

Reaction equation

HRID 474143 reaction equation
[Cl:1][C:2]1[C:3]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][N:7]=1.[C:18](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:12][CH:13]=2)=[N:4][CH:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59535937[4-(3-Chloropyrazin-2-yl)phenyl]acetic acid

Product 1

HCID 59535943Methyl 2-(4-(3-chloropyrazin-2-yl)phenyl)acetateYield 36%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.40 g (1.6 mmol) of [4-(3-chloropyrazin-2-yl)phenyl]acetic acid in 3.0 mL of DMF was added 0.67 g (4.8 mmol) of potassium carbonate and 0.14 mL (2.3 mmol) iodomethane. After 1 h at 40° C., the reaction mixture was cooled, diluted with CH2Cl2, washed three times with water followed by brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (silica gel, linear gradient 0-75% EtOAc in hexanes) afforded 0.15 g (36%) methyl [4-(3-chloropyrazin-2-yl)phenyl]acetate. ES-MS M+1=263.0.

Workup

  1. temperaturethe reaction mixture was cooled
  2. washwashed three times with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (silica gel, linear gradient 0-75% EtOAc in hexanes)

Sources & evidence

ORD record
ord-8afcbd229ef94af1a1223a59477f9308
Source dataset
uspto-grants-2014_01
Patent number
US08637513B2

Linked notes

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