Acetic Anhydride → N-{2-bromo-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]benzyl}acetamide

HRID 1873474Notes

Reaction equation

HRID 1873474 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[CH2:9][C:10]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[CH2:11][N:12]=2)[CH:5]=[CH:4][C:3]=1[CH2:25][NH2:26].[C:27](OC(=O)C)(=[O:29])[CH3:28]>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[CH2:9][C:10]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:14])([F:15])[F:16])[CH2:11][N:12]=2)[CH:5]=[CH:4][C:3]=1[CH2:25][NH:26][C:27](=[O:29])[CH3:28]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 580921092-(4-aminomethyl-3-bromophenyl)-4-(3,5-dichlorophenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrole

Product 1

HCID 44183261N-{2-bromo-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]benzyl}acetamideYield 61.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-bromo-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]phenyl)methanamine (0.15 g) in THF (10 ml) was added acetic anhydride (0.04 g), and the mixture was stirred for 1 hour at room temperature. The mixture was concentrated under reduced pressure to give residual material which was purified by silica gel chromatography, to obtain N-{2-bromo-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]benzyl}acetamide (0.1 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto give residual material which
  3. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-b45bd45126db49e883eca973af04bd11
Source dataset
uspto-grants-2012_11
Patent number
US08304371B2

Reaction notes

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