1,3-Dibromopropane → 3-(4-Chlorophenyl)-2-isopropyl-4-oxo-9,10-dihydro-4H,8H-1,11-dioxa-7-aza-cyclohepta[a]naphthalene-7-carbaldehyde

HRID 14472Notes

Reaction equation

HRID 14472 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[C:12]([OH:22])[C:13]([NH:19][CH:20]=[O:21])=[CH:14][CH:15]=3)[O:10][C:9]=2[CH:23]([CH3:25])[CH3:24])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:33][CH2:34][CH2:35]Br>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17](=[O:18])[C:16]3[CH:15]=[CH:14][C:13]4[N:19]([CH:20]=[O:21])[CH2:35][CH2:34][CH2:33][O:22][C:12]=4[C:11]=3[O:10][C:9]=2[CH:23]([CH3:25])[CH3:24])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 10796Cesium carbonateHCID 59724241N-[3-(4-Chlorophenyl)-8-hydroxy-2-isopropyl-4-oxo-4H-chromen-7-yl]formamide

Product 1

HCID 866256113-(4-Chlorophenyl)-2-isopropyl-4-oxo-9,10-dihydro-4H,8H-1,11-dioxa-7-aza-cyclohepta[a]naphthalene-7-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of N-[3-(4-chlorophenyl)-8-hydroxy-2-isopropyl-4-oxo-4H-chromen-7-yl]formamide (0.122 g, 0.34 mmol), cesium carbonate (0.444 g, 1.36 mmol, 4 eq.) and 1,3-dibromopropane (0.069 g, 0.34 mmol) in anhydrous N,N-dimethylformamide (3 ml) is heated at 60° C. under a nitrogen atmosphere for 2 h. The mixture is cooled to room temperature and filtered through Celite filter aid. The pad of Celite is washed with ethyl acetate and methylene chloride, and the combined filtrates are evaporated in vacuo to afford a brown solid. This is purified by flash chromatography (cyclohexane/ethyl acetate=9:1 to 4:1) to furnish the title compound as a yellow solid.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. filtrationfiltered through Celite
  3. filtrationfilter aid
  4. washThe pad of Celite is washed with ethyl acetate and methylene chloride
  5. customthe combined filtrates are evaporated in vacuo
  6. customto afford a brown solid
  7. customThis is purified by flash chromatography (cyclohexane/ethyl acetate=9:1 to 4:1)

Sources & evidence

ORD record
ord-15d3387fbc6a4af686b9091a3582fd51
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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