Triethylamine → 6-[6-[(trimethylsilanyl)ethynyl]-pyridin-3-yl]-pyrido[2',1':2,3]-imidazo[4,5-c]isoquinolin-5(6H)-one

HRID 1670694Notes

Reaction equation

HRID 1670694 reaction equation
C(N(CC)CC)C.[CH3:8][Si:9]([C:12]#[CH:13])([CH3:11])[CH3:10].Br[C:15]1[N:20]=[CH:19][C:18]([N:21]2[C:30]3[N:31]4[CH:37]=[CH:36][CH:35]=[CH:34][C:32]4=[N:33][C:29]=3[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]2=[O:38])=[CH:17][CH:16]=1>CN(C=O)C.[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>[CH3:8][Si:9]([C:12]#[C:13][C:15]1[N:20]=[CH:19][C:18]([N:21]2[C:30]3[N:31]4[CH:37]=[CH:36][CH:35]=[CH:34][C:32]4=[N:33][C:29]=3[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]2=[O:38])=[CH:17][CH:16]=1)([CH3:11])[CH3:10]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 247710936-(6-bromo-pyridin-3-yl)-pyrido-[2',1':2,3]imidazo[4,5-c]isoquinolin-5(6H)-one

Product 1

HCID 577670226-[6-[(trimethylsilanyl)ethynyl]-pyridin-3-yl]-pyrido[2',1':2,3]-imidazo[4,5-c]isoquinolin-5(6H)-oneYield 96%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst2×HCID 178418476HCID 178418476, compoundCatalyst2×HCID 6228DimethylformamideSolvent

Procedure

CuI (0.2 equiv., 0.256 mmol, 0.049 g), dichlorobis(triphenylphosphine)-palladium(II) (0.1 equiv., 0.13 mmol, 0.090 g), triethylamine (1.0 equiv., 1.28 mmol, 0.129 g), (trimethylsilyl)acetylene (10.0 equiv., 12.8 mmol, 1.26 g) and KI (10.0 equiv., 12.8 mmol, 2.12 g) were added to a mixture of 6-(6-bromo-pyridin-3-yl)-pyrido-[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one (21) (1.0 equiv., 1.28 mmol, 0.50 g) in dry DMF (10 ml). The reaction mixture was stirred at room temperature under N2 atmosphere for 24 h. After addition of a second portion of CuI (0.20 equiv., 0.256 mmol, 0.049 g) and dichlorobis(triphenylphosphine)-palladium(II) (0.1 equiv., 0.13 mmol, 0.090 g), the reaction mixture was further stirred at 60° C. for 17 h. The solvent was evaporated under reduced pressure and the pasty residue was mixed with dichloromethane and washed with water. The organic layer was evaporated under reduced pressure and the residue purified by column chromatography (ethyl acetate/heptane 60:40) to afford 6-[6-[(trimethylsilanyl)ethynyl]-pyridin-3-yl]-pyrido[2′,1′:2,3]-imidazo[4,5-c]isoquinolin-5(6H)-one (I9) (0.50 g, yield=96%, purity (LC)=95%).

Workup

  1. stirringthe reaction mixture was further stirred at 60° C. for 17 h
  2. customThe solvent was evaporated under reduced pressure
  3. additionthe pasty residue was mixed with dichloromethane
  4. washwashed with water
  5. customThe organic layer was evaporated under reduced pressure
  6. customthe residue purified by column chromatography (ethyl acetate/heptane 60:40)

Sources & evidence

ORD record
ord-c774a75f6db64060bee37906934b4d3f
Source dataset
uspto-grants-2011_08
Patent number
US07994187B2

Reaction notes

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