1,2-Dimethoxyethane → HCID 9858363, compound

HRID 2183690Notes

Reaction equation

HRID 2183690 reaction equation
I[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[CH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1.C(COC)OC.[Cl:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)C>[Cl:24][C:25]1[CH:30]=[C:29]([C:2]2[CH:11]=[C:10]3[C:5]([C:6]([N:13]4[CH2:17][CH2:16][CH2:15][CH2:14]4)=[CH:7][C:8]([CH3:12])=[N:9]3)=[CH:4][CH:3]=2)[CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 113366637-Iodo-2-methyl-4-pyrrolidin-1-yl-quinoline

Product 1

HCID 9858363HCID 9858363, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1.5 g 7-iodo-2-methyl-4-pyrrolidin-1-yl-quinoline (Example 3.1), 256 tetrakis(triphenylphosphine) palladium and 30 ml Dimethoxyethane is stirred under argon for 15 min. 1.04 g 3-Chlorophenylboronic acid and 7 ml Ethanol are added. The resulting red solution is stirred for another 10 min. at room temperature and treated afterwards with 19 ml of a 2M aqueous solution of sodium carbonate. The mixture is refluxed for 1.5 h under vigorous stirring. After the reaction is complete, the reaction mixture is concentrated on a rotary evaporator. The residue is taken up in 50 ml water and extracted twice with 50 ml ethyl acetate. The combined organic phases are washed with 50 ml saturated aqueous solution of sodium chloride, dried over magnesium sulfate and filtered. The filtrate is evaporated and the residue is chromatographed on silica gel (eluent: Dichloromethane/Methanol 19:1 then 4:1). The pure fractions are combined and evaporated. 1.235 g of 7-(3-Chloro-phenyl)-2-methyl-4-pyrrolidin-1-yl-quinoline are obtained as a colorless oil. MS (ISP): 323.3 (M+H)+.

Workup

  1. stirringThe resulting red solution is stirred for another 10 min. at room temperature
  2. temperatureThe mixture is refluxed for 1.5 h under vigorous stirring
  3. concentrationthe reaction mixture is concentrated on a rotary evaporator
  4. extractionextracted twice with 50 ml ethyl acetate
  5. washThe combined organic phases are washed with 50 ml saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate is evaporated
  9. customthe residue is chromatographed on silica gel (eluent
  10. customevaporated

Sources & evidence

ORD record
ord-284bf39f016a4c33a0ecfa06c483882a
Source dataset
uspto-grants-2005_05
Patent number
US06900226B2

Reaction notes

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