Diethylamine → HCID 67323462, compound

HRID 882078Notes

Reaction equation

HRID 882078 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:12])=[N:7]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(NCC)C.[CH3:37][Si:38]([C:41]#[CH:42])([CH3:40])[CH3:39]>[Cu](I)I.CN(C=O)C>[CH3:12][C:6]1[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[C:42]#[C:41][Si:38]([CH3:40])([CH3:39])[CH3:37])[N:7]=1

Participants

7

Reactant 4

HCID 8021DiethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 122313065-BROMO-2-METHYLQUINOLINE

Product 1

HCID 67323462HCID 67323462, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

In a sealed tube were introduced 5-bromo-2-methyl-quinoline (1.0 g, 4.5 mmol, 1.0 eq), PdCl2(PPh3)3 (154 mg, 0.22 mmol, 5% mol), copper iodide (42 mg, 0.22 mmol, 5% mol), and triphenylphosphine (236 mg, 0.9 mmol, 20% mol). Then, DMF (10 mL) was added followed by diethylamine (9.5 mL, 68 mmol, 15 eq) and trimethylsilylacetylene (700 μL, 5.0 mmol, 1.1 eq). The mixture was heated at 110° C. overnight. After cooling down the solvent was evaporated and the crude product was purified by column chromatography (Florisil, Cyclohexane-EtOAc 95:5) to afford 2-methyl-5-trimethylsilanylethynyl-quinoline as a white solid (970 mg, 90%).

Workup

  1. temperatureAfter cooling down the solvent
  2. customwas evaporated
  3. customthe crude product was purified by column chromatography (Florisil, Cyclohexane-EtOAc 95:5)

Sources & evidence

ORD record
ord-373e3ef8e53444809705ba5a94fb2ec0
Source dataset
uspto-grants-2015_03
Patent number
US08993767B2

Reaction notes

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