N-bromobutanimide → HCID 58565357, compound

HRID 2175335Notes

Reaction equation

HRID 2175335 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:11]=[C:12]([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[C:17]2[CH:25]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH3:26])[CH:13]=[CH:14][CH:15]=1>CN(C=O)C.O>[Br:1][C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:16]([C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([F:9])[CH:11]=2)[C:17]=1[CH:25]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH3:26]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 58565341HCID 58565341, compound

Product 1

HCID 58565357HCID 58565357, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-bromosuccinimide (0.24 g, 1.3 mmol) in DMF (1 mL) was added dropwise to an ice-cooled solution of tert-butyl {1-[1-(3-fluorophenyl)-1H-indol-2-yl]ethyl}carbamate (0.41 g, 1.2 mmol) in N,N-dimethylformamide (5 mL) The resulting mixture was allowed to warm to room temperature and stirred for an additional 4 hours. The mixture was diluted with water and extracted with EtOAc. The extracts were combined, dried over MgSO4, concentrated, and purified on silica gel (eluting with 0-10% EtOAc/hexane) to give the desired product (0.34 g, 68%). LCMS calculated for C21H22BrFN2O2Na(M+Na)+: m/z=455.1. Found: 455.0.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. custompurified on silica gel (eluting with 0-10% EtOAc/hexane)

Sources & evidence

ORD record
ord-cbc1c5f835a24064b3e8eb03426d6085
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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