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

HRID 1895962
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HRID 1895962 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 214133-BromoquinolineHCID 2724141Tetrabutylammonium FluorideHCID 866273353-Nitro-2-(4-prop-2-ynylidenepiperidin-1-yl)pyridine

생성물 1

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

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매
HCID 962Water용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a5c2853921794869a277bcd2cfb95654
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08518916B2

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