N-bromobutanimide → HCID 59032964, compound

HRID 1634714Notes

Reaction equation

HRID 1634714 reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[Br:19]N1C(=O)CCC1=O>CN(C)C=O>[Br:19][C:9]1[C:10]2[NH:11][C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]=2[C:6]([O:5][CH2:4][C@@H:2]2[CH2:3][O:1]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 10879208(S)-(+)-4-(2,3-Epoxypropoxy)carbazole

Product 1

HCID 59032964HCID 59032964, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-[(2S)-oxiranylmethoxy]-9H-carbazole (0.750 g, 3.13 mmol) and N-bromosuccinimide (0.57 g, 3.2 mmol) in 10 mL dry dimethylformamide (DMF) was stirred at ambient temperature for 48 hours. The reaction mixture was partitioned with EtOAc and H2O. The organic phase was washed with H2O and dried with Na2SO4. The solvent was removed (rotovap) and the residue purified by flash chromatography (hexane-EtOAc 5:1) afforded 0.10 g of the title compound.

Workup

  1. customThe reaction mixture was partitioned with EtOAc and H2O
  2. washThe organic phase was washed with H2O
  3. dry with materialdried with Na2SO4
  4. customThe solvent was removed (rotovap)
  5. customthe residue purified by flash chromatography (hexane-EtOAc 5:1)

Sources & evidence

ORD record
ord-6a6055ec7e90482aac559e9c310f8a1d
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

Loading…