HCID 9977862, compound → HCID 10449844, compound

HRID 1672347Notes

Reaction equation

HRID 1672347 reaction equation
Br[C:2]1[N:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[C:4]2[C:13]3[CH:12]=[C:11]([Cl:14])[CH:10]=[CH:9][C:8]=3[N:7]=[CH:6][C:5]=2[N:15]=1.[C:23]([Cu])#[N:24]>[C-]#N.C([N+](CC)(CC)CC)C.O1CCOCC1.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].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:14][C:11]1[CH:10]=[CH:9][C:8]2[N:7]=[CH:6][C:5]3[N:15]=[C:2]([C:23]#[N:24])[N:3]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[Cl:22])[C:4]=3[C:13]=2[CH:12]=1

Participants

7

Reactant 2

HCID 9977862HCID 9977862, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 10449844HCID 10449844, compound

Reagents, catalysts & solvents 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 3014735Tetraethylammonium cyanideCatalystHCID 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 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

In an alternative way, the title compound is prepared from 2-bromo-8-chloro-1-(2-chloro-phenyl)-1H-imidazo[4,5-c]quinoline (50 mg, 0.13 mmol; Example 82), CuCN (68 mg, 0.76 mmol; Fluka, Buchs, Switzerland), tris(dibenzylideneacetone)dipalladium chloroform adduct (Pd2(dba)3.CHCl3; 20 mg, 0.02 mmol; Aldrich), 1,1′-bis(diphenylphosphino)ferrocene (DPPF; 45 mg, 0.08 mmol; Aldrich), and tetraethylammonium cyanide (40 mg, 0.25 mmol; Fluka, Buchs, Switzerland) in 5 ml 1,4-dioxane by heating the reaction mixture for 5 h at 140° C. in a sealed tube.

Sources & evidence

ORD record
ord-cacd1eb95f2a4ab09f67cad597a937ef
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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