Potassium Carbonate → 2-(4-Fluoro-3-methyl-phenylamino)-hexanoic acid methyl ester

HRID 885500Notes

Reaction equation

HRID 885500 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH:4](Br)[CH2:5][CH2:6][CH2:7][CH3:8].[F:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][C:13]=1[CH3:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:10])[CH:4]([NH:16][C:15]1[CH:17]=[CH:18][C:12]([F:11])=[C:13]([CH3:19])[CH:14]=1)[CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 679814-Fluoro-m-toluidineHCID 95578Hexanoic acid, 2-bromo-, methyl ester

Product 1

HCID 691697822-(4-Fluoro-3-methyl-phenylamino)-hexanoic acid methyl esterYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromo-hexanoic acid methyl ester (0.500 g, 2.404 mmol) and 4-fluoro-3-methylaniline (0.301 g, 2.404 mmol) in 15 mL of DMF, was added K2CO3 (1.661 g, 12.020 mmol). After stirring at room temperature under N2 for 88 h, the reaction mixture was diluted with 60 mL of water and extracted with dichloromethane (60 mL×3). The organic extracts were combined dried over anhydrous Na2SO4 and the solvent removed under reduced pressure. Flash chromatography (silica gel) eluting with 0-20% ethyl acetate/hexanes afforded the title compound as brown oil (0.273 g, 45% yield). LC-MS: tR=9.9 min; m/z 254 (M+H)+.

Workup

  1. extractionextracted with dichloromethane (60 mL×3)
  2. dry with materialThe organic extracts were combined dried over anhydrous Na2SO4
  3. customthe solvent removed under reduced pressure
  4. washFlash chromatography (silica gel) eluting with 0-20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e2915520c606496aaa3ffa9e9ad42f01
Source dataset
uspto-grants-2012_08
Patent number
US08242174B2

Reaction notes

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