1,2-Dibromoethane → 9-Acetyl-1,2-dihydro-6-(2-bromoethyl)-cyclopenta[c]carbazole-3-one

HRID 1615038Notes

Reaction equation

HRID 1615038 reaction equation
[H-].[Na+].[C:3]([C:6]1[CH:18]=[CH:17][C:16]2[NH:15][C:14]3[CH:13]=[CH:12][C:11]4[C:19](=[O:22])[CH2:20][CH2:21][C:10]=4[C:9]=3[C:8]=2[CH:7]=1)(=[O:5])[CH3:4].[H][H].[Br:25][CH2:26][CH2:27]Br>CN(C=O)C>[C:3]([C:6]1[CH:18]=[CH:17][C:16]2[N:15]([CH2:27][CH2:26][Br:25])[C:14]3[CH:13]=[CH:12][C:11]4[C:19](=[O:22])[CH2:20][CH2:21][C:10]=4[C:9]=3[C:8]=2[CH:7]=1)(=[O:5])[CH3:4]

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 585448999-Acetyl-1,2-dihydrocyclopenta[c]carbazol-3(6H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 585449069-Acetyl-1,2-dihydro-6-(2-bromoethyl)-cyclopenta[c]carbazole-3-oneYield 35.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (2 g of 60%, 50 mmol) was added to a suspension of compound 91 (4 g, 15.2 mmol) in dry DMF (100 mL), and the mixture was stirred at room temperature about 1 h until the evolution of hydrogen ceased. 1,2-dibromethane (20 g, 106 mmol) was added in dropwise under nitrogen. The reaction mixture was stirred for 30 min at room temperature, then at 60° C. for 24 h, and poured into ice water (300 mL). The precipitated grey solid was filtered off and the crude product purified by column chromatography (CHCl3) to give 2 g of starting material and about 1 g (2.7 mmol, 35.5% from converted material) of the alkylated carbazole 92 as a cream solid.

Workup

  1. waitat 60° C. for 24 h
  2. filtrationThe precipitated grey solid was filtered off
  3. customthe crude product purified by column chromatography (CHCl3)

Sources & evidence

ORD record
ord-94eda7f35b5c47efb3f04ee014d9cf4a
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

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