O-Xylene → HCID 22502825, compound

HRID 1006897Notes

Reaction equation

HRID 1006897 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.[OH-:20].[Na+].C1(C)[C:23](C)=[CH:24][CH:25]=[CH:26][CH:27]=1>>[CH2:18]([N:15]1[CH2:16][CH2:17][N:12]([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:11]=[C:2]([C:11]3[CH:10]=[CH:5][C:4]([N:12]4[CH2:23][CH2:24][CH:25]([OH:20])[CH2:26][CH2:27]4)=[N:3][CH:2]=3)[N:3]=2)[CH2:13][CH2:14]1)[CH3:19]

Participants

4

Reactant 3

HCID 7237O-XyleneHCID 14798Sodium HydroxideHCID 225024471-(1-Ethylpiperazin-4-yl)-3-bromoisoquinoline

Product 1

HCID 22502825HCID 22502825, compound

Procedure

3-Bromo-1-(4-ethylpiperazin-1-yl)isoquinoline (1.16 g) and {2-[4-(t-butyldimethyloxy)piperidin-1-yl]pyridin-5-yl}tributylstannum (1.37 g) was reacted in the presence of tetrakistriphenylphosphine dichloride (0.30 g) in xylene (30 ml) at 140° C. for 5 hr. The reaction solution was concentrated. A 2N aqueous solution of hydrochloric acid was added to the resulting residue, and then reacted at 50° C. for 1 hr. The reaction solution was basified with a 2N aqueous solution of sodium hydroxide, and then it was extracted with ethyl acetate. The resulting organic layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to give 0.26 g of the free compound of the title compound as a colorless amorphous.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionA 2N aqueous solution of hydrochloric acid was added to the resulting residue
  3. customreacted at 50° C. for 1 hr
  4. extractionit was extracted with ethyl acetate
  5. washThe resulting organic layer was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-75780b1969314cf78788d7b283f35fb0
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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