Diethylamine → 1315248-52-2

HRID 882082Notes

Reaction equation

HRID 882082 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]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:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:42]#[C:41][Si:38]([CH3:40])([CH3:39])[CH3:37])[CH:3]=2)[N:8]=1

Participants

7

Reactant 4

HCID 8021DiethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 5228856-Bromo-2-methylquinoline

Product 1

HCID 673240081315248-52-2Yield 83.5%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Procedure

In a sealed tube were introduced 6-bromo-2-methyl-quinoline (4.6 g, 21 mmol, 1 eq), PdCl2(PPh3)3 (727 mg, 1 mmol, 5% mol), copper iodide (197 mg, 1 mmol, 5% mol), and triphenylphosphine (1.1 g, 4.1 mmol, 20% mol). Then, DMF (35 mL) was added followed by diethylamine (6 mL, 62 mmol, 5 eq) and trimethylsilylacetylene (3.2 mL, 23 mmol, 1.1 eq). The mixture was refluxed overnight. After cooling down the solvent was evaporated and the crude product was purified by column chromatography (Florisil, Cyclohexane-AcOEt 95/5) and obtained as a white solid (4.2 g, 83%).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. temperatureAfter cooling down the solvent
  3. customwas evaporated
  4. customthe crude product was purified by column chromatography (Florisil, Cyclohexane-AcOEt 95/5)

Sources & evidence

ORD record
ord-04c055a8faff44718962cc9babfb7dcc
Source dataset
uspto-grants-2015_03
Patent number
US08993767B2

Reaction notes

Loading…