1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 4'-Methyl-5-(2-oxo-2,3-dihydro-indol-1-yl)-biphenyl-3-carboxylic acid methyl ester

HRID 2406897노트

반응식

HRID 2406897 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[CH:8]=[C:9]([NH:11][C:12](=[O:21])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2Br)[CH:10]=1)=[O:4].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[CH:8]=[C:9]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][C:12]2=[O:21])[CH:10]=1)=[O:4]

참가 물질

5

반응물 2

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 596277535-[2-(2-Bromo-phenyl)-acetylamino]-4'-methyl-biphenyl-3-carboxylic acid methyl ester

생성물 1

HCID 596277454'-Methyl-5-(2-oxo-2,3-dihydro-indol-1-yl)-biphenyl-3-carboxylic acid methyl ester

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

The 5-[2-(2-bromo-phenyl)-acetylamino]-4′-methyl-biphenyl-3-carboxylic acid methyl ester from step 1 was dissolved in toluene (3 mL) and CsCO3 (325 mg, 1 equive.), Pd(OAc)2 (15 mg) and XANTPHOS (59 mg) were added. The reaction mixture was stirred overnight at 100° C., then cooled and partitioned between water and ethyl acetate. The organic layer was separated and concentrated under reduced pressure, and the residue was purified by preparative thin layer chromatography (2:1 hexanes:ethyl acetate) to give 4′-methyl-5-(2-oxo-2,3-dihydro-indol-1-yl)-biphenyl-3-carboxylic acid methyl ester, which was used directly in the next step.

후처리

  1. temperaturecooled
  2. custompartitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was purified by preparative thin layer chromatography (2:1 hexanes:ethyl acetate)

출처 및 근거

ORD 기록
ord-553b7a82ba394cbf8115306c02d3ca44
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809402B2

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