1-(1-Ethylpiperazin-4-yl)-3-bromoisoquinoline → HCID 22503240, compound

HRID 1814458Notes

Reaction equation

HRID 1814458 reaction equation
Br[C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH3:19])[CH2:14][CH2:13]2)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:20]1[CH2:48][O:47][C:22]2([CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][C:31]([Sn](CCCC)(CCCC)CCCC)=[CH:30][CH:29]=3)[CH2:24][CH2:23]2)[O:21]1>C1(C)C(C)=CC=CC=1>[CH2:20]1[CH2:48][O:47][C:22]2([CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][C:31]([C:2]4[N:3]=[C:4]([N:12]5[CH2:17][CH2:16][N:15]([CH2:18][CH3:19])[CH2:14][CH2:13]5)[C:5]5[C:10]([CH:11]=4)=[CH:9][CH:8]=[CH:7][CH:6]=5)=[CH:30][CH:29]=3)[CH2:24][CH2:23]2)[O:21]1

Participants

4

Reactant 2

HCID 225024471-(1-Ethylpiperazin-4-yl)-3-bromoisoquinolineHCID 86594635HCID 86594635, compound

Product 1

HCID 22503240HCID 22503240, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

3-Bromo-1-(4-ethylpiperazin-1-yl)isoquinoline (1.72 g) and 4-(4,4-ethylenedioxypiperidin-1-yl)phenyltributylstannum (3.12 g) were reacted in the presence of tetrakistriphenylphosphine dichloride (0.5 g) in xylene (50 ml) at 140° C. for 5 hr. The reaction solution was concentrated, and ethyl acetate and an aqueous saturated solution of sodium bicarbonate were added to the resulting residue, for partitioning. The resulting organic layer was washed with water and brine, dried over magnesium sulfate and evaporated. The resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to give 1.27 g of title compound as a white powder.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionethyl acetate and an aqueous saturated solution of sodium bicarbonate were added to the resulting residue
  3. customfor partitioning
  4. washThe resulting organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-39b2d3dc464a464c8542c29718b9118a
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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