N-bromobutanimide → HCID 22676785, compound

HRID 1006245Notes

Reaction equation

HRID 1006245 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:20]2)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN(C)C=O>[CH2:9]([O:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:20]2[Br:1])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 95721Ethyl 5-(phenylmethoxy)-1H-indole-2-carboxylate

Product 1

HCID 22676785HCID 22676785, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of N-bromosuccinimide (7.83 g, 44.0 mmol) in N,N-dimethylformamide (30 mL) was added dropwise (40 min) to a cooled (0 ° C.) and stirred solution of ethyl 5-(benzyloxy)-1H-indole-2-carboxylate (10.0 g, 39.2 mmol) in N,N-dimethylformamide (20 mL). The cold bath was removed and stirring was continued for an additional 1.5 h. The reaction was poured over ice water (600 mL) and the resulting precipitate was collected by vacuum filtration. The precipitate was washed with water and dried to give 12.9 g (98%) of crude product. This material was used in the next reaction without further purification or analysis.

Workup

  1. customThe cold bath was removed
  2. additionThe reaction was poured over ice water (600 mL)
  3. filtrationthe resulting precipitate was collected by vacuum filtration
  4. washThe precipitate was washed with water
  5. customdried

Sources & evidence

ORD record
ord-8660644fd1e04f81a1ccacfaed201257
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

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