N-bromobutanimide → HCID 21867514, compound

HRID 857329Notes

Reaction equation

HRID 857329 reaction equation
[CH3:1][S:2][C:3]1[C:4]2[C:5]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)=[CH:6][NH:7][C:8]=2[CH:9]=[CH:10][CH:11]=1.C1C(=O)N([Br:27])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[CH3:1][S:2][C:3]1[C:4]2[C:5]([CH2:12][C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)=[C:6]([Br:27])[NH:7][C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 21867506HCID 21867506, compound

Product 1

HCID 21867514HCID 21867514, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the indole of Step 6 (700 mg, 2.4 mmol) in CCl4 (15 mL) was added NBS (475 mg, 2.7 mmol). The reaction mixture was heated to 50° C. and stirred for 20 minutes. The resulting suspension was filtered on SiO2 pad eluted with 50% EtOAc in hexanes and concentrated. The title compound was obtained in quantitative yield as a brownish solid foam and used as such.

Workup

  1. filtrationThe resulting suspension was filtered on SiO2 pad
  2. washeluted with 50% EtOAc in hexanes
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ae7560e23b8c4785996aaf3d5209711e
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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