3-Bromoquinoline → 6-(Quinolin-3-yl)hex-5-yn-1-ol

HRID 1583432Notes

Reaction equation

HRID 1583432 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:12]([OH:18])[CH2:13][CH2:14][CH2:15][C:16]#[CH:17]>ClCCl.C(N(CC)CC)C.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>[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[C:2]([C:17]#[C:16][CH2:15][CH2:14][CH2:13][CH2:12][OH:18])[CH:3]=1

Participants

6

Reactant 2

HCID 214133-BromoquinolineHCID 702345-Hexyn-1-ol

Product 1

HCID 135575496-(Quinolin-3-yl)hex-5-yn-1-olYield 89%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

6-(3-Quinolinyl)-5-hexyn-1-ol was prepared in the manner described above in Example 105 starting with 15.0 g of 3-bromoquinoline, 8.5 g of 5-hexyn-1-ol, 1.05 g of bis(triphenylphosphine)palladium dichloride and 0.10 g of cuprous iodide in 115 ml of dichloromethane and 28.5 ml of triethylamine. The crude product was chromatographed on a preparative high pressure liquid chromatograph eluting with 2.5% methanol-dichloromethane to give 14.4 g (89%) of 6-(3-quinolinyl)-5-hexyn-1-ol as a colorless oil. A portion was purified further on a silica thick layer plate eluting with 10% methanol-dichloromethane and solidified on drying, mp 47°-48° C.

Workup

  1. custom6-(3-Quinolinyl)-5-hexyn-1-ol was prepared in the manner
  2. customThe crude product was chromatographed on a preparative high pressure liquid chromatograph
  3. washeluting with 2.5% methanol-dichloromethane

Sources & evidence

ORD record
ord-dc9815920bc94b30bf5eaba1eb2bbdb8
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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