Tri(butyl)vinyltin → 1-{4-Nitro-2-[(1E)-prop-1-en-1-yl]phenyl}-3-vinylpyridin-2(1H)-one

HRID 452235ノート

反応式

HRID 452235 の反応式
Br[C:2]1[C:3](=[O:20])[N:4]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=2/[CH:17]=[CH:18]/[CH3:19])[CH:5]=[CH:6][CH:7]=1.[CH2:21](C([Sn])=C(CCCC)CCCC)[CH2:22]CC>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:14]([C:11]1[CH:12]=[CH:13][C:8]([N:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH:21]=[CH2:22])[C:3]2=[O:20])=[C:9](/[CH:17]=[CH:18]/[CH3:19])[CH:10]=1)([O-:16])=[O:15]

参加物

5

反応物 2

HCID 53438229Tri(butyl)vinyltinHCID 595366023-Bromo-1-{4-nitro-2-[(1E)-prop-1-en-1-yl]phenyl}pyridin-2(1H)-one

生成物 1

HCID 595366061-{4-Nitro-2-[(1E)-prop-1-en-1-yl]phenyl}-3-vinylpyridin-2(1H)-one

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

929 mg (2.77 mmol) of the compound from Example 44A are dissolved in 14 ml of anhydrous dioxane, and 64 mg (0.06 mmol) of tetrakis(triphenylphosphine)palladium(0) are added. At room temperature, 1.06 g (3.33 mmol) of tributylvinyl tin are added slowly, and, after the addition has ended, the mixture is heated at reflux for 21 h. The reaction solution is allowed to cool and is filtered through kieselguhr. The filter cake is then washed with ethyl acetate, and the combined organic filtrates are concentrated to dryness under reduced pressure. The product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate=4:1). This gives 568 mg (70% of theory) of the desired product.

後処理

  1. additionafter the addition
  2. temperaturethe mixture is heated
  3. temperatureat reflux for 21 h
  4. temperatureto cool
  5. filtrationis filtered through kieselguhr
  6. washThe filter cake is then washed with ethyl acetate
  7. concentrationthe combined organic filtrates are concentrated to dryness under reduced pressure
  8. customThe product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-aecc5967a9a8404b803d2a744469ff20
出典データセット
uspto-grants-2013_07
特許番号
US08487111B2

反応ノート

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