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Triphenylarsine → 5-Trifluoromethyl-6-vinyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

HRID 225593
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HRID 225593 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:18]([F:21])([F:20])[F:19])=[C:13](I)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22]1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:23]=1.C([Sn](CCCC)(CCCC)CCCC)=C>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][C:10]2[C:15](=[CH:14][C:13]([CH:22]=[CH2:23])=[C:12]([C:18]([F:21])([F:20])[F:19])[CH:11]=2)[CH2:16]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 11773TriphenylarsineHCID 81998TributylvinyltinHCID 57753490HCID 57753490, 화합물

생성물 1

HCID 577533965-Trifluoromethyl-6-vinyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester수율 93%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매
HCID 31275
1,4-Dioxane
용매

실험 절차

To a stirred solution 0.61 mmol 5-iodo-6-trifluoromethyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (Example A35(d)) in 3 ml dioxane were added 0.04 mmol palladium(II) acetate and 0.18 mmol triphenylarsine and the mixture was stirred at RT for 10 min. 0.91 mmol vinyltributylstannane was then added and the mixture was heated at 100° C. for 16 h. The reaction mixture was then cooled to room temperature, filtered, and the filtrate was concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a yellow solid (93% yield). MS (m/e): 258.0 ([M+H−Me2C═CH2]+, 100%).

후처리

  1. temperaturethe mixture was heated at 100° C. for 16 h
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by chromatography (SiO2, heptane/ethyl acetate)

출처 및 근거

ORD 기록
ord-6cfc6bcee5bc40f29157f71ecbf9c848
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07557114B2

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