N-bromobutanimide → N-Trifluoroacetyl-7-(4-bromo-2-Methyl-2H-pyrazol-3-yl)-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 84122Notes

Reaction equation

HRID 84122 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[CH:14][C:15]([C:17]3[N:18]([CH3:22])[N:19]=[CH:20][CH:21]=3)=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4].[Br:25]N1C(=O)CCC1=O>ClCCl>[F:24][C:2]([F:1])([F:23])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[CH:14][C:15]([C:17]3[N:18]([CH3:22])[N:19]=[CH:20][C:21]=3[Br:25])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22292810N-Trifluoroacetyl-7-(2-Methyl-2H-pyrazol-3-yl)-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 22292801N-Trifluoroacetyl-7-(4-bromo-2-Methyl-2H-pyrazol-3-yl)-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepineYield 108.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-trifluoroacetyl-7-(2-Methyl-2H-pyrazol-3-yl)-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (30 mg, 0.082 mmol) in dichloromethane (1 mL) was treated with N-bromosuccinimide (15.3 mg, 0.086 mmol) and stirred overnight at 20 C. The product mixture was absorbed on silica and purified by flash chromatography (2-5% MeOH in CH2Cl2, silica) resulting in 37 mg of a white crystalline solid. MS calculated for C17H17BrF3N3O+H: 416, observed: 416.

Workup

  1. customThe product mixture was absorbed on silica
  2. custompurified by flash chromatography (2-5% MeOH in CH2Cl2, silica)

Sources & evidence

ORD record
ord-665650e6d4ec430bb5cf55eb70831971
Source dataset
uspto-grants-2014_09
Patent number
US08846906B2

Reaction notes

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