N-bromobutanimide → HCID 23152327, compound

HRID 1012270Notes

Reaction equation

HRID 1012270 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[N:11][C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:27]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:27][C:8]1[N:9]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:10]2=[N:11][C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:13][CH:14]=[C:15]2[C:7]=1[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 23152701HCID 23152701, compound

Product 1

HCID 23152327HCID 23152327, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of ethyl 3-cyclohexyl-1-ethoxycarbonylmethyl-1H-pyrrolo[2,3-b]pyridine-6-carboxylate (463 mg, 1.34 mmol) in carbon tetrachloride (10 ml) was added N-bromosuccinimide (287 mg, 1.61 mmol), and the mixture was heated under reflux for 4 hr. The mixture was allowed to cool to room temperature and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate-5:1) to give ethyl 2-bromo-3-cyclohexyl-1-ethoxycarbonylmethyl-1H-pyrrolo[2,3-b]pyridine-6-carboxylate (457 mg, yield 64%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hr
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate-5:1)

Sources & evidence

ORD record
ord-09c5f4eafe33415ca42082ad841df6d4
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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