Bromine → N-(3,5-Bis-trifluoromethyl-benzyl)-N-(9-bromo-7-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamide

HRID 2353917Notes

Reaction equation

HRID 2353917 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[CH2:6][N:7]([CH:11]1[CH2:17][CH2:16][CH2:15][NH:14][C:13]2[CH:18]=[CH:19][C:20]([C:22]([F:25])([F:24])[F:23])=[CH:21][C:12]1=2)[C:8](=[O:10])[CH3:9].[Br:35]Br>CC(O)=O>[F:30][C:29]([F:31])([F:32])[C:27]1[CH:26]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:33])[F:34])[CH:28]=1)[CH2:6][N:7]([CH:11]1[CH2:17][CH2:16][CH2:15][NH:14][C:13]2[C:18]([Br:35])=[CH:19][C:20]([C:22]([F:23])([F:24])[F:25])=[CH:21][C:12]1=2)[C:8](=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 24408BromineHCID 86616072N-(3,5-Bis-trifluoromethyl-benzyl)-N-(7-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamide

Product 1

HCID 86616074N-(3,5-Bis-trifluoromethyl-benzyl)-N-(9-bromo-7-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamideYield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of crude N-(3,5-Bis-trifluoromethyl-benzyl)-N-(7-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamide (0.0980 mg, 0.197 mmol) in HOAc (2.00 ml), was added bromine (0.0106 ml, 0.207 mmol) dropwise. The reaction mixture was stirred at room temperature overnight. Remove the solvent on a rotary evaporator. Purification by silica gel chromatography (eluent, 0-40% ethyl acetate in hexane) provided the titled compound (0.0850 mg, 75%). MS (ES+): 577, 579 (M+H).

Workup

  1. customRemove the solvent
  2. customon a rotary evaporator
  3. customPurification by silica gel chromatography (eluent, 0-40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d2e6b9637aff4aad8375738f0c8123da
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

Loading…