Triethylamine → HCID 69080535, compound

HRID 2404987Notes

Reaction equation

HRID 2404987 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([F:11])([F:10])[F:9].C(N(CC)CC)C.[CH2:19]([C:21]1[N:22]([CH2:34][C:35]#[CH:36])[C:23]2[C:32]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[N:26]=[CH:25][C:24]=2[N:33]=1)[CH3:20]>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd].[Cu]I>[CH2:19]([C:21]1[N:22]([CH2:34][C:35]#[C:36][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8]([F:11])([F:10])[F:9])[C:23]2[C:32]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[N:26]=[CH:25][C:24]=2[N:33]=1)[CH3:20]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 67957Benzene, 1-iodo-2-(trifluoromethyl)-HCID 86626641HCID 86626641, compound

Product 1

HCID 69080535HCID 69080535, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 6228DimethylformamideSolvent

Procedure

Tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (64.5 mg, 0.03 eq.), 2-iodobenzotrifluoride (321 μL, 1.1 eq.), triethylamine (869 μL, 3.0 eq.), and copper (I) iodide (23.7 mg, 0.06 eq.) were added sequentially to a solution of 2-ethyl-1-(2-propynyl)-1H-imidazo[4,5-c]quinoline (489 mg, 2.08 mmol, 1.0 eq.) in DMF (10.6 mL). The reaction mixture was stirred at ambient temperature for 18 hours and then concentrated under reduced pressure. The residue was purified by column chromatography (silica gel eluting with 3/97 methanol/chloroform) to provide 0.13 g of 2-ethyl-1-[3-(2-trifluoromethylphenyl)-2-propynyl]-1H-imidazo[4,5-c]quinoline as a light yellow solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by column chromatography (silica gel eluting with 3/97 methanol/chloroform)

Sources & evidence

ORD record
ord-fcc53e962fc94a168734b1e1da227ed8
Source dataset
uspto-grants-2014_08
Patent number
US08802853B2

Reaction notes

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