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Ethyl 4-iodobenzoate → Ethyl 4-[(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-1-isopropyl-7-quinolinyl)ethynyl]benzoate

HRID 52452
Notes
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Reaction equation

HRID 52452 reaction equation
[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[CH:13])=[CH:9][CH:10]=2)[N:5]([CH:14]([CH3:16])[CH3:15])[C:4](=[O:17])[CH2:3]1.I[C:20]1[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=1>C(NCC)C.[Cu]I.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>[CH3:18][C:2]1([CH3:1])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[C:13][C:20]3[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=3)=[CH:9][CH:10]=2)[N:5]([CH:14]([CH3:15])[CH3:16])[C:4](=[O:17])[CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 142891Ethyl 4-iodobenzoateHCID 199637207-Ethynyl-4,4-dimethyl-1-(propan-2-yl)-3,4-dihydroquinolin-2(1H)-one2×

Product 1

HCID 19963709Ethyl 4-[(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-1-isopropyl-7-quinolinyl)ethynyl]benzoate

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst
HCID 178418476
HCID 178418476, compound
Catalyst
HCID 8021DiethylamineSolvent

Procedure

To a solution of 0.282 g (1.17 mmol) of 4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-1-iso-propyl-7-ethynyl quinoline (Compound 30) and 0.52 g (1.9 mmol) of ethyl 4-iodobenzoate in 2.5 ml of diethylamine which was degassed under argon for 30 min, was added 0.049 g (0.26 mmol) of copper(I) iodide and then 0.159 g (0.23 mmol) of bis(triphenylphosphine)palladium(II) chloride. The reaction was stirred at room temperature for 4 h. The reaction mixture was then concentrated in vacuo. Purification by flash chromatography (silica, 10% ethyl acetate in hexane) gave the title compound as a solid.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customPurification by flash chromatography (silica, 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-f670bde99aa84cfc9e4ceb313be1e03c
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05616712

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes