Triethylamine → 4-[6-(4-Chloro-phenyl)-quinoline-2-ylethynyl]-benzaldehyde

HRID 1916752Notes

Reaction equation

HRID 1916752 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[CH:8]=2)[N:3]=1.[C:19]([C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=1)#[CH:20].C(N(CC)CC)C>CN(C=O)C.C(#N)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>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[N:3]=[C:2]([C:20]#[C:19][C:21]2[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=2)[CH:11]=[CH:10]3)=[CH:13][CH:14]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 27716454-EthynylbenzaldehydeHCID 859696922-Bromo-6-(4-chloro-phenyl)-quinoline

Product 1

HCID 859696974-[6-(4-Chloro-phenyl)-quinoline-2-ylethynyl]-benzaldehyde

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

Under a nitrogen atmosphere 0.6 mg CuI, 9.3 mg Pd(PPh3)2Cl2 and 318 mg (1 mmol) 2-bromo-6-(4-chloro-phenyl)-quinoline are added successively to a solution of 85 mg (0.66 mmol) 4-ethynyl-benzaldehyde and 2.6 mL (18.67 mmol) triethylamine in 5 mL absolute DMF and 10 mL acetonitrile. The reaction mixture is stirred for 14 hours at RT and evaporated down. The purification is carried out by column chromatography on silica gel (PE/EtOAc 1:1).

Workup

  1. customevaporated down
  2. customThe purification

Sources & evidence

ORD record
ord-1fdbf28f2ce44200932e9ee827c1caea
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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