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

HRID 225593
ノート
印刷プレビュー

反応式

HRID 225593 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11773TriphenylarsineHCID 81998TributylvinyltinHCID 57753490HCID 57753490、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒
HCID 31275
1,4-Dioxane
溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-6cfc6bcee5bc40f29157f71ecbf9c848
出典データセット
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07557114B2

反応ノート

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