Dichloromethane → 4,4-Dimethyl-6-trimethylsilylethynyl-1,2,3,4-tetrahydroquinoline

HRID 1707615Notes

Reaction equation

[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[C:9](Br)[CH:10]=2)[NH:5][CH2:4][CH2:3]1.[CH3:14][Si:15]([C:18]#[CH:19])([CH3:17])[CH3:16].C(Cl)Cl>C(N(CC)CC)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:19]#[C:18][Si:15]([CH3:17])([CH3:16])[CH3:14])[CH:10]=2)[NH:5][CH2:4][CH2:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 1.608 g (6.7 mmol) of 4,4-dimethyl-6-bromo-1,2,3,4-tetrahydroquinoline in 1.5 ml of triethylamine in a heavy-walled tube was degassed under argon and then treated with 75 mg (0.39 mmol) of cuprous iodide and 150 mg (0.21 mmol) of bis(triphenylphosphine) palladium (II) chloride. The mixture was degassed again under argon, treated with 2.09 g (21.2 mmol) of trimethylsilylacetylene and the tube was sealed. The mixture was heated at 50° C. for 48 hours. After cooling to room temperature methylene chloride was added to the reaction mixture and the mixture filtered. The filtrate was concentrated in vacuo and the residue purified by flash chromatography (silica; 10% ethyl acetate in hexanes) to give the title compound as a yellow oil.

Workup

customThe mixture was degassed again under argon
customthe tube was sealed
additionwas added to the reaction mixture
filtrationthe mixture filtered
concentrationThe filtrate was concentrated in vacuo
customthe residue purified by flash chromatography (silica; 10% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-60e9602669f54b3c8e9281c1ebd69856
Source dataset: uspto-grants-1994_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05354752

Reaction notes

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