Water → Ethyl[1-(2-bromophenyl)-8-chloro-4-oxo-1,2,4,5-tetrahydrobenzo[d]azepin-3-yl]acetate

HRID 1444823Notes

Reaction equation

HRID 1444823 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:14][NH:13][C:12](=[O:15])[CH2:11][C:10]2[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:9]1=2.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].O>CN(C)C=O>[CH2:32]([O:31][C:29](=[O:30])[CH2:28][N:13]1[C:12](=[O:15])[CH2:11][C:10]2[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:9]=2[CH:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])[CH2:14]1)[CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 590255435-(2-Bromophenyl)-7-chloro-1,3,4,5-tetrahydrobenzo[d]azepin-2-one

Product 1

HCID 59025541Ethyl[1-(2-bromophenyl)-8-chloro-4-oxo-1,2,4,5-tetrahydrobenzo[d]azepin-3-yl]acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1500 mg of the compound from Example 10A (4.28 mol) are dissolved in 30 ml of dimethylformamide, and 2788 mg of caesium carbonate (8.56 mol) are added. 0.95 ml of ethyl bromoacetate (1429 mg, 8.56 mol) is added drop wise, and the suspension is stirred at room temperature overnight. Water is added, and the mixture is extracted three times with dichloromethane. The combined organic phases are dried over sodium sulphate and concentrated in a rotary evaporator. The residue is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5). 450 mg (24% of theory) of the title compound are obtained.

Workup

  1. extractionthe mixture is extracted three times with dichloromethane
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. concentrationconcentrated in a rotary evaporator
  4. customThe residue is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5)

Sources & evidence

ORD record
ord-e431760daf7f4391abfebedafa5ab891
Source dataset
uspto-grants-2010_02
Patent number
US07662956B2

Reaction notes

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