N-bromobutanimide → HCID 59198429, compound

HRID 1896508Notes

Reaction equation

HRID 1896508 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH:11]=[CH:12][NH:13][C:14](=[O:15])[C:5]=3[C:4]=2[CH:3]=1.[Al].C1C(=O)N([Br:24])C(=O)C1>CN(C=O)C.CCOC(C)=O>[Br:24][C:11]1[C:6]2[NH:7][C:8]3[CH:9]=[CH:10][C:2]([F:1])=[CH:3][C:4]=3[C:5]=2[C:14](=[O:15])[NH:13][CH:12]=1

Participants

6

Reactant 3

HCID 67184N-bromobutanimideHCID 5359268AluminumHCID 59198430HCID 59198430, compound

Product 1

HCID 59198429HCID 59198429, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

8-Fluoro-2,5-dihydro-1H-pyrido[4,3-b]indol-1-one (10 g, 49 mmol) was dissolved in 400 mL DMF and covered with aluminum foil. NBS was added in a single portion and the solution was stirred for 1 hr at which time the reaction mixture was diluted with EtOAc, washed with water, brine, dried over MgSO4, filtered, concentrated. The crude residue purified on silica gel and eluted with EtOAc/hexanes (0 to 75% gradient elution).

Workup

  1. washwashed with water, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue purified on silica gel
  6. washeluted with EtOAc/hexanes (0 to 75% gradient elution)

Sources & evidence

ORD record
ord-cffbadaefe9747319ff91892ee5aa2b2
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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