2-Methylquinoline → HCID 66598438, compound

HRID 422355Notes

Reaction equation

HRID 422355 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

5

Reactant 3

HCID 70602-MethylquinolineHCID 6425893-Bromo-1-(trimethylsilyl)-1-propyneHCID 2724682Lithium diisopropylamide

Product 1

HCID 66598438HCID 66598438, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

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

Sources & evidence

ORD record
ord-3c651f8445aa49279d7c6c5346361ebe
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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