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

HRID 885500노트

반응식

HRID 885500 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-e2915520c606496aaa3ffa9e9ad42f01
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242174B2

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