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3-Bromoquinoline → 3-{3-[1-(3-Nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl}quinoline

HRID 1895962
ノート
印刷プレビュー

反応式

HRID 1895962 の反応式
[N+:1]([C:4]1[C:5]([N:10]2[CH2:15][CH2:14][C:13](=[CH:16][C:17]#[CH:18])[CH2:12][CH2:11]2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Br[C:20]1[CH:21]=[N:22][C:23]2[C:28]([CH:29]=1)=[CH:27][CH:26]=[CH:25][CH:24]=2.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[N+:1]([C:4]1[C:5]([N:10]2[CH2:15][CH2:14][C:13](=[CH:16][C:17]#[C:18][C:20]3[CH:21]=[N:22][C:23]4[C:28]([CH:29]=3)=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:12][CH2:11]2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O: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 214133-BromoquinolineHCID 2724141Tetrabutylammonium FluorideHCID 866273353-Nitro-2-(4-prop-2-ynylidenepiperidin-1-yl)pyridine

生成物 1

HCID 866273373-{3-[1-(3-Nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl}quinoline収率 655.7%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒
HCID 962Water溶媒

実験手順

A well homogenised mixture of the Compound 1c (50 mg, 0.21 mmol), 3-bromoquinoline (0.039 ml, 0.21 mmol), bis-(triphenylphosphine)palladium dichloride (5 mg, 0.007 mmol) and tetra-butylammonium fluoride (215 mg, 0.82 mmol) was stirred at 80° C. for 1 h in a sealed vessel. The reaction mixture was cooled, poured into water and extracted with EtOAc. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by flash chromatography (EtOAc—Petroleum Ether gradient from 2:8 to 4:6) affording the title product (0.51 g).

後処理

  1. stirringwas stirred at 80° C. for 1 h in a sealed vessel
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. customdried on Na2SO4
  6. customevaporated to dryness in vacuo
  7. customto afford a residue, which
  8. customwas purified by flash chromatography (EtOAc—Petroleum Ether gradient from 2:8 to 4:6)

出典と根拠

ORDレコード
ord-a5c2853921794869a277bcd2cfb95654
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08518916B2

反応ノート

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