N-bromobutanimide → HCID 67291282, compound

HRID 511854Notes

Reaction equation

HRID 511854 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([CH3:17])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:18]([O:20][CH3:21])=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:29])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:29][CH2:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[CH:10]=[C:9]([C:18]([O:20][CH3:21])=[O:19])[N:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 67289108HCID 67289108, compound

Product 1

HCID 67291282HCID 67291282, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of methyl 1-tert-butoxycarbonyl-4-methylindole-2-carboxylate (0.13 g, 0.48 mmol), NBS (0.087 g, 0.48 mmol), and AIBN (4 mg, 0.024 mmol) in carbon tetrachloride (1.9 mL) was heated to reflux for 3 h. The reaction mixture was cooled to room temperature and filtered and washed with carbon tetrachloride. The filtrate was evaporated to give a yellow oil that was purified by silica gel chromatography (EtOAc:hexane=8:92) to give 0.12 g (72% yield) of the title compound as a pale yellow solid:

Workup

  1. temperatureto reflux for 3 h
  2. filtrationfiltered
  3. washwashed with carbon tetrachloride
  4. customThe filtrate was evaporated
  5. customto give a yellow oil that
  6. customwas purified by silica gel chromatography (EtOAc:hexane=8:92)

Sources & evidence

ORD record
ord-ae9339fc6f3a4756ba770ed23eed66d8
Source dataset
uspto-grants-2015_08
Patent number
US09101616B2

Reaction notes

Loading…