1-Bromo-2-Chloroethane → 3-(2-(4-(2-Chloroethoxy)benzyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-N-cyclopropyl-4-methylbenzamide

HRID 907270Notes

Reaction equation

HRID 907270 reaction equation
[CH:1]1([NH:4][C:5](=[O:32])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[N:18]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=3)[CH:17]=[CH:16]4)[CH:7]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:40][CH2:41][Cl:42]>C(#N)C>[Cl:42][CH2:41][CH2:40][O:31][C:28]1[CH:27]=[CH:26][C:25]([CH2:24][N:18]2[CH:17]=[CH:16][C:15]3[C:20](=[CH:21][CH:22]=[C:13]([C:8]4[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=4[CH3:12])[C:5]([NH:4][CH:1]4[CH2:2][CH2:3]4)=[O:32])[CH:14]=3)[C:19]2=[O:23])=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 57551752N-Cyclopropyl-3-(2-(4-hydroxybenzyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-4-methylbenzamide

Product 1

HCID 575518303-(2-(4-(2-Chloroethoxy)benzyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-N-cyclopropyl-4-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of the product of step i) (0.33 g), potassium carbonate (1.07 g) and 1-bromo-2-chloroethane (1.12 g) in acetonitrile (10 mL) was heated at reflux for 38 hours. The reaction mixture was concentrated to dryness and the residue partitioned between dichloromethane and water. The organics were collected and purified (SiO2, 9:1 dichloromethane:methanol) to give the sub-title compound (0.31 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 38 hours
  3. concentrationThe reaction mixture was concentrated to dryness
  4. customthe residue partitioned between dichloromethane and water
  5. customThe organics were collected
  6. custompurified (SiO2, 9:1 dichloromethane:methanol)

Sources & evidence

ORD record
ord-d8a9f3cfa5984c1492372e2a1ac49e0a
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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