2-Methylquinoline → 2-(4-Trimethylsilanyl-but-3-ynyl)-quinoline

HRID 1189159Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Li+].CC([N-]C(C)C)C.Br[CH2:21][C:22]#[C:23][Si:24]([CH3:27])([CH3:26])[CH3:25]>C1COCC1>[CH3:25][Si:24]([CH3:27])([CH3:26])[C:23]#[C:22][CH2:21][CH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

2-Methyl-quinoline (0.28 mL, 2.09 mmol) was added dropwise to a solution of LDA (3.0 mL, 0.8 M in THF) in THF (3 mL) at −78° C. and the reaction mixture was stirred for 1 hour at −78° C. Then (3-bromo-prop-1-ynyl)-trimethyl-silane (0.39 mL, 2.51 mmol) was added to the reaction mixture, the solution was stirred for 18 hours at room temperature and was quenched with water. The aqueous phase was extracted with DCM. The organic phase was washed with water, dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 9:1) to yield 338 mg (1.33 mmol, 64%) of 2-(4-trimethylsilanyl-but-3-ynyl)-quinoline as a yellow solid.

Workup

stirringthe solution was stirred for 18 hours at room temperature
customwas quenched with water
extractionThe aqueous phase was extracted with DCM
washThe organic phase was washed with water
dry with materialdried over MgSO4
filtrationfiltered
customevaporated
customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 9:1)

Sources & evidence

ORD record: ord-6454f2626c284450a6dd623b40e419a5
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674106B2

Reaction notes

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