3-Fluoroaniline → (4-Fluoro-phenyl)-(3-fluoro-phenylamino)-acetic acid

HRID 1044033

반응식

HRID 1044033 반응식
Br[CH:2]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[F:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17]>C(#N)C.CCOC(C)=O>[F:12][C:9]1[CH:10]=[CH:11][C:6]([CH:2]([NH:17][C:16]2[CH:18]=[CH:19][CH:20]=[C:14]([F:13])[CH:15]=2)[C:3]([OH:5])=[O:4])=[CH:7][CH:8]=1

참가 물질

5

반응물 2

HCID 97423-Fluoroaniline2회HCID 16217752Bromo(4-fluorophenyl)acetic acid

생성물 1

HCID 54890833(4-Fluoro-phenyl)-(3-fluoro-phenylamino)-acetic acid수율 90.1%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

A mixture of 2-bromo-2-(4-fluorophenyl)acetic acid (500 mg, 2.15 mmol) and 3-fluoroaniline (477 mg, 4.29 mmol) in acetonitrile (8 ml) was heated under microwave irradiation at 100° C. for 50 minutes. Then 3-fluoroaniline (238 mg, 2.15 mmol) was added again, and the reaction mixture was heated at 120° C. for 45 minutes in a microwave oven (UPLC-MS monitoring: complete conversion). The organic solution was diluted with EtOAc and was washed with 2N HCl and then with brine. The organic phase was dried over Na2SO4, filtered and the solvent was evaporated to give 2-(4-fluorophenyl)-2-(3-fluorophenylamino)acetic acid (510 mg, 90% yield).

후처리

  1. temperaturethe reaction mixture was heated at 120° C. for 45 minutes in a microwave oven (UPLC-MS monitoring: complete conversion)
  2. washwas washed with 2N HCl
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-00e485c4da9d42d0b1ddd573c2dd10c1
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563577B2

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