Triethylamine → 4,4-Dimethyl-2-oxo-1,2,3,4-tetrahydro-7-[(trimethylsilyl)ethynyl]quinoline

HRID 52446Notes

Reaction equation

HRID 52446 reaction equation
[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][C:8](Br)=[CH:9][CH:10]=2)[NH:5][C:4](=[O:13])[CH2:3]1.C(N(CC)CC)C.CC1(C)C2C(=CC=C([C:33]#[C:34][Si:35]([CH3:38])([CH3:37])[CH3:36])C=2)NC(=O)C1>[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>[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][C:8]([C:33]#[C:34][Si:35]([CH3:38])([CH3:37])[CH3:36])=[CH:9][CH:10]=2)[NH:5][C:4](=[O:13])[CH2:3]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 199637077-Bromo-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one2×HCID 19963711HCID 19963711, compound2×

Product 1

HCID 199637324,4-Dimethyl-2-oxo-1,2,3,4-tetrahydro-7-[(trimethylsilyl)ethynyl]quinolineYield 74%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

2.2398 g (8.8 mmol) of 4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-7-bromoquinoline (Compound 18), 371 mg (1.9 mmol) of CuI, 1.087 g (1.5 mmol) of Pd(PPh3)2Cl2, 35 ml (0.251 mol) of triethylamine and 4.0 ml (28.0 mmol) of trimethylacetylene were reacted substantially in accordance with the procedure used for the preparation of 4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-6-[(trimethylsilyl)ethynyl]quinoline (Compound 2) to give the title compound as pale orange solids (74%).

Sources & evidence

ORD record
ord-cc3be286e8cd48f59b1ed630a6448864
Source dataset
uspto-grants-1997_04
Patent number
US05616712

Reaction notes

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