Benzoyl Peroxide → HCID 86617364, compound

HRID 642406Notes

Reaction equation

HRID 642406 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:22])=[C:8]2[C:14]([Cl:15])=[C:13]([Cl:16])[N:12]([CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].[Br:23]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:22])=[C:8]2[C:14]([Cl:15])=[C:13]([Cl:16])[N:12]([CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[C:9]2=[C:10]([Br:23])[N:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 68426392HCID 68426392, compound

Product 1

HCID 86617364HCID 86617364, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension of 2,3-dichloro-4-hydroxy-1-(3-methyl-butyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (2.23 g, 6.46 mmol), N-bromosuccinimide (1.38 g, 7.75 mmol), and benzoyl peroxide (156 mg, 0.646 mmol) in 50 mL of benzene was heated at reflux temperature for 5 hours. The reaction mixture was washed successively with saturated sodium bicarbonate, brine, saturated ammonium chloride solution, and brine. The organic solution was dried, filtered, and concentrated. The crude product was purified by flash chromatography eluting from silica gel with a gradient of 0-2% ethyl acetate in hexanes to produce 1.36 g of a white solid. MS: (+) m/z 423.1 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 5 hours
  3. washThe reaction mixture was washed successively with saturated sodium bicarbonate, brine, saturated ammonium chloride solution, and brine
  4. customThe organic solution was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography
  8. washeluting from silica gel with a gradient of 0-2% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-684a54b8890b41a9a05eb4ef358c2011
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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