Phenol → HCID 22396996, compound

HRID 1071034Notes

Reaction equation

HRID 1071034 reaction equation
[C:1]([N:9]1[CH2:22][CH2:21][C:20]2[C:19]3[CH:18]=[C:17](Br)[CH:16]=[CH:15][C:14]=3[NH:13][C:12]=2[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]1([OH:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC1C=CC=CC=1C.[Cu-]=O>[C:1]([N:9]1[CH2:22][CH2:21][C:20]2[C:19]3[CH:18]=[C:17]([O:30][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:16]=[CH:15][C:14]=3[NH:13][C:12]=2[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 22396998HCID 22396998, compound

Product 1

HCID 22396996HCID 22396996, compoundYield 10.6%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 7237O-XyleneSolvent

Procedure

A mixture of 3-benzoyl-9-bromo-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (1.00 g, 2.71 mmol), phenol (0.51 g, 5.42 mmol), copper(I) oxide (0.019 g, 0.14 mmol), and cesium carbonate (2.65 g, 8.12 mmol) in o-xylene was refluxed for 24 h. After cooling to room temperature, the mixture was filtered and washed with ethyl acetate. The filtrate was concentrated in vacuo to dryness, and the residue was subjected to column chromatography (silica gel, 60% EtOAc/hexane) to afford 0.11 g (10%) of a colorless solid as the title compound: 1H NMR (300 MHz, CDCl3) δ 7.42, 7.29-7.19, 7.03-6.86, 4.12-3.91, 3.72-3.61, 3.20-3.04, 2.90-2.76; MS (ESI+) m/z 383 (M++1).

Workup

  1. temperaturewas refluxed for 24 h
  2. filtrationthe mixture was filtered
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-b75dc10bbf4544ef8c3047697698785d
Source dataset
uspto-grants-2005_06
Patent number
US06903090B2

Reaction notes

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