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

HRID 1895962Notes

Reaction equation

HRID 1895962 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-a5c2853921794869a277bcd2cfb95654
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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