Triethylamine → 6-(4-Chloro-phenyl)-2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-quinoline

HRID 1916757Notes

Reaction equation

HRID 1916757 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:34]=[CH:33][C:24]([O:25][CH2:26][CH2:27][N:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)=[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:22]=[CH:23][C:24]([O:25][CH2:26][CH2:27][N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:33][CH:34]=2)[CH:11]=[CH:10]3)=[CH:13][CH:14]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 859696922-Bromo-6-(4-chloro-phenyl)-quinolineHCID 859698151-[2-(4-Ethynyl-phenoxy)-ethyl]-pyrrolidine

Product 1

HCID 598358386-(4-Chloro-phenyl)-2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-quinoline

Reagents, catalysts & solvents 4

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

Procedure

In 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 142 mg (0.66 mmol) 1-[2-(4-ethynyl-phenoxy)-ethyl]-pyrrolidine and 2.6 mL (18.67 mmol) triethylamine in 5 mL absolute DMF and 10 mL acetonitrile. The reaction mixture is stirred for 14 h at RT and evaporated down. The purification is carried out by column chromatography on silica gel (DCM/MeOH/NH3 90:10:1).

Workup

  1. customevaporated down
  2. customThe purification

Sources & evidence

ORD record
ord-edafc43fbf92438a81c863e1df397e43
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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