Bromoacetyl bromide → 1-(4-{6-[2-(Benzyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl]-4-propylpyridin-3-yl}piperazin-1-yl)-2-bromoethanone

HRID 1038553Notes

Reaction equation

HRID 1038553 reaction equation
[CH2:1]([O:8][C:9]([C:18]1[N:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[C:20]([CH2:30][CH2:31][CH3:32])[CH:19]=1)([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:33][CH2:34][C:35](Br)=[O:36]>ClCCl>[CH2:1]([O:8][C:9]([C:18]1[N:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][N:27]([C:35](=[O:36])[CH2:34][Br:33])[CH2:26][CH2:25]2)=[C:20]([CH2:30][CH2:31][CH3:32])[CH:19]=1)([C:10]([F:11])([F:12])[F:13])[C:14]([F:16])([F:15])[F:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 61147Bromoacetyl bromideHCID 866471981-{6-[2-(Benzyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl]-4-propylpyridin-3-yl}piperazine

Product 1

HCID 866471991-(4-{6-[2-(Benzyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl]-4-propylpyridin-3-yl}piperazin-1-yl)-2-bromoethanoneYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-{6-[2-(Benzyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl]-4-propylpyridin-3-yl}piperazine (27 mg, 0.0563 mmol) was dissolved in dichloromethane (1.0 mL). Under ice-cold conditions, N,N′-dimethylaniline (15 μL, 0.118 mmol) and bromoacetylbromide (5.1 μL, 0.0591 mmol) were added, and the mixture was stirred under ice-cold conditions for 20 minutes. The reaction solution was concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/acetone), and the title compound (25 mg (yield 78%)) was obtained as a yellow oil.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. customThe obtained residue was purified by silica-gel column chromatography (hexane/acetone)

Sources & evidence

ORD record
ord-dd1a9590ceea4942a12386d34c694948
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

Loading…