N-bromobutanimide → HCID 90412119, compound

HRID 1521949Notes

Reaction equation

HRID 1521949 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:30][CH3:31])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([CH:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]4)=[CH:16][C:9]=23)[CH:7]=1.[Br:32]N1C(=O)CCC1=O>CN(C)C=O.O.C(OCC)(=O)C>[Br:32][C:16]1[C:9]2[C:10](=[N:11][CH:12]=[CH:13][C:8]=2[C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:30][CH3:31])[NH:14][C:15]=1[CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[CH2:19][CH2:18]1

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 90412965HCID 90412965, compound

Product 1

HCID 90412119HCID 90412119, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Example 17F (300 mg, 0.705 mmol) in N,N-dimethylformamide (3 mL) at 0° C. was added N-bromosuccinimide (188 mg, 1.058 mmol) and the mixture was stirred at room temperature for 3 hours. The mixture was diluted with water and ethyl acetate and the ethyl acetate layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated. Purification by column chromatography (silica gel, 15% ethyl acetate in hexane) afforded the title compound. LCMS: 506 (M+3)+.

Workup

  1. washthe ethyl acetate layer was washed with water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by column chromatography (silica gel, 15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-acdc2788d552480ab41009db732af940
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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