Methanol → HCID 18669096, compound

HRID 1058968Notes

Reaction equation

HRID 1058968 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[C:5]([C:13]([F:16])([F:15])[F:14])[CH:4]=1.[Cl:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)=[C:21]2[CH2:34][CH2:35][C:36]([N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1)=[O:37].C(=O)([O-])[O-].[K+].[K+].CO>CC(C)=O.C(OCC)(=O)C>[F:14][C:13]([F:16])([F:15])[C:5]1[CH:4]=[C:3]([CH2:2][N:41]2[CH2:42][CH2:43][N:38]([C:36](=[O:37])[CH2:35][CH2:34][C:21]3[C:20]4[C:24](=[CH:25][CH:26]=[C:18]([Cl:17])[CH:19]=4)[NH:23][C:22]=3[C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)[CH2:39][CH2:40]2)[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 1225733,5-Bis(trifluoromethyl)benzyl bromideHCID 18669068HCID 18669068, compound

Product 1

HCID 18669096HCID 18669096, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(Bromomethyl)-3,5-bis(trifluoromethyl)benzene (83 mg) was added to a mixture of 1-{3-[5-chloro-2-(4-chlorophenyl)-1H-indol-3-yl]-1-oxopropyl}piperazine (Description 30, 35 mg) and potassium carbonate (36 mg) in acetone (3 mL) and the mixture was stirred at room temperature for 2 h. Methanol (1 mL) and ethyl acetate (10 mL) were added and the mixture was washed with water. The organic fraction was filtered through a plug of silica in a Bond Elut™ cartridge, eluting with hexane/EtOAc (80:20 increasing to 60:40), to give the title compound as a colorless solid (49 mg, 89%). 1H NMR (360 MHz, CDCl3) δ2.16-2.19 (2H, m), 2.33-2.36 (2H, m), 2.59-2.63 (2H, m), 3.15-3.20 (2H, m), 3.28-3.30 (2H, m), 3.53 (2H, s), 3.58-3.61 (2H, m), 7.13 (1H, dd, J 8.7, 1.8 Hz), 7.25 (1H, d, J 8.3 Hz), 7.36-7.53 (6H, m), 7.77 (2H, s), and 8.51 (1H, s). m/z (ES+) 628, 630 (M+1).

Workup

  1. washthe mixture was washed with water
  2. filtrationThe organic fraction was filtered through a plug of silica in a Bond Elut™ cartridge
  3. washeluting with hexane/EtOAc (80:20 increasing to 60:40)

Sources & evidence

ORD record
ord-919195bbba4845948c0f0e5c0d5031f6
Source dataset
uspto-grants-2003_02
Patent number
US06518273B1

Reaction notes

Loading…