Triethylamine → HCID 69076756, compound

HRID 2404988Notes

Reaction equation

HRID 2404988 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:18]([C:20]1[N:21]([CH2:34][C:35]#[CH:36])[C:22]2[C:31]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[N:25]=[C:24](N)[C:23]=2[N:33]=1)[CH3:19]>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>[CH2:18]([C:20]1[N:21]([CH2:34][C:35]#[C:36][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[C:22]2[C:31]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[N:25]=[CH:24][C:23]=2[N:33]=1)[CH3:19]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 124951-Iodo-4-nitrobenzeneHCID 86626642HCID 86626642, compound

Product 1

HCID 69076756HCID 69076756, compoundYield 37.4%

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 (95 mg, 0.03 eq.), 4-iodonitrobenzene (0.84 g, 1.1 eq.), triethylamine (0.92 g, 3 eq.), and copper (I) iodide (35 mg, 0.06, eq.) were added sequentially to a solution of 2-ethyl-1-(2-propynyl)-1H-imidazo[4,5-c]quinolin-4-amine (0.72 g, 3.0 mmol, 1.0 eq.) in DMF. The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane (30 mL) and water (50 mL). The organic layer was separated, washed twice with water, and then concentrated under reduced pressure to a solid. This material was purified by column chromatography (silica gel eluting with 3/97 methanol/dichloromethane) to provide 0.4 g of 2-ethyl-1-[3-(4-nitrophenyl)-2-propynyl]-1H-imidazo[4,5-c]quinoline.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between dichloromethane (30 mL) and water (50 mL)
  3. customThe organic layer was separated
  4. washwashed twice with water
  5. concentrationconcentrated under reduced pressure to a solid
  6. customThis material was purified by column chromatography (silica gel eluting with 3/97 methanol/dichloromethane)

Sources & evidence

ORD record
ord-770e9b43ebc545b79223d6e5fd24fc41
Source dataset
uspto-grants-2014_08
Patent number
US08802853B2

Reaction notes

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