Benzene, (2-bromoethoxy)- → HCID 22396720, compound

HRID 2307044Notes

Reaction equation

HRID 2307044 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[CH:11]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18][CH:12]3[NH:13][C:14]=2[CH:15]=[CH:16][CH:17]=1.[C:30]1([O:36][CH2:37][CH2:38]Br)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[CH:11]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18][CH:12]3[N:13]([CH2:38][CH2:37][O:36][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:14]=2[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 68526Benzene, (2-bromoethoxy)-HCID 516892Sodium BicarbonateHCID 22396753HCID 22396753, compound

Product 1

HCID 22396720HCID 22396720, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 10-(2,4-dichlorophenyl)-1,4,5,5a,6,10b-hexahydroazepino[4,5-b]indole-3(2H)-carboxylate (54 mg) in DMF (1.2 ml) was added KH (10 mg) and 2-bromoethyl phenyl ether (30 mg). The reaction mixture was stirred 24 h, poured into satd NaHCO3, extracted with CH2Cl2, dried over MgSO4, filtered and concentrated. Purification via flash chromatography provided the title compound: 1H NMR (CDCl3) δ 1.63, 2.30-2.50, 2.92, 3.14, 3.42, 3.75, 4.26, 4.53, 6.84, 6.96, 7.20-7.51.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification via flash chromatography

Sources & evidence

ORD record
ord-132f3d94a1744bfdb609e22aa1b8e899
Source dataset
uspto-grants-2004_12
Patent number
US06828314B2

Reaction notes

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