N-bromobutanimide → HCID 22624309, compound

HRID 279066Notes

Reaction equation

HRID 279066 reaction equation
[C:1]([C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=2[F:21])[N:9]=1)=[O:6])([CH3:4])([CH3:3])[CH3:2].[Br:22]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[C:1]([C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][Br:22])=[CH:16][C:15]=2[F:21])[N:9]=1)=[O:6])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22624311HCID 22624311, compound

Product 1

HCID 22624309HCID 22624309, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a 250 mL round-bottomed flask equipped with condenser and N2 inlet were added 5.0 g (17.48 mmol) N-t-butylcarbonyl-6-(2-fluoro-4-methylphenyl)-pyridin-2-ylamine (Example 2B), 4.36 g (24.47 mmol) N-bromosuccinimide, 10 mg azobisdi-(1,1-dimethylcyclohexyl)nitrile, and 85 mL carbon tetrachloride. The reaction was refluxed under a heat lamp for 30 min, cooled, and filtered. The filtrate was concentrated and chromatographed on silica gel using hexane/ethyl acetate as eluant to afford 5.36 g (52%) of the product as an oil, which was crystallized from isopropanol to give mp 97-100° C.

Workup

  1. customTo a 250 mL round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was refluxed under a heat lamp for 30 min
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customchromatographed on silica gel

Sources & evidence

ORD record
ord-9720735743484e8384a99e9479fc45e6
Source dataset
uspto-grants-2002_03
Patent number
US06362195B1

Reaction notes

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