N-bromobutanimide → HCID 53837501, compound

HRID 865649Notes

Reaction equation

HRID 865649 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:24]N1C(=O)CCC1=O>C1COCC1.CCOCC>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[CH:15]=2)[C:10]([Br:24])=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 54064886HCID 54064886, compound

Product 1

HCID 53837501HCID 53837501, compoundYield 103%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution under N2 of 6-(4-fluorophenyl)indole-1-carboxylic acid t-butyl ester (2.00 g, 6.42 mmol), prepared as in step 1, in THF (36 mL) was added N-bromosuccinimide (1.26 g, 7.08 mmol) in a single portion and the clear-orange solution was stirred overnight at ambient temperature. The reaction mixture was diluted with ether (500 mL) and extracted with aqueous NaHSO3 (1-2M, 250 mL) and saturated aqueous NaHCO3. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo to give a viscous, clear-yellow oil (2.58 g) , which solidified on standing.

Workup

  1. extractionextracted with aqueous NaHSO3 (1-2M, 250 mL) and saturated aqueous NaHCO3
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-35445d9d93ba42d495d099bb75b22a39
Source dataset
uspto-grants-1996_10
Patent number
US05567711

Reaction notes

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