HCID 22627483, compound → HCID 18784032, compound

HRID 278130Notes

Reaction equation

HRID 278130 reaction equation
C[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH2:13])=[O:12])=[CH:8][CH:9]=2)[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Br:21])[C:3]=1[CH2:22][CH2:23][CH3:24].C1C=C[NH+]=CC=1.[Br:31][Br-]Br>ClCCl.N1C=CC=CC=1.C(OCC)(=O)C>[Br:31][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH2:13])=[O:12])=[CH:8][CH:9]=2)[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Br:21])[C:3]=1[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 1

HCID 22627483HCID 22627483, compound

Product 1

HCID 18784032HCID 18784032, compoundYield 54.3%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of methyl 1-(2-bromobenzyl)-2-propylindole-6-carboxamide (52 mg) in a mixture of dichloromethane (3 ml) and pyridine (1 ml) was added pyridinium bromide perbromide (50 mg), and the mixture was stirred at 0° C. for 1.5 hours. The resulting mixture was diluted with ethyl acetate and washed with diluted hydrochloric acid, aqueous sodium bicarbonate and brine, then dried over sodium sulfate and evaporated in vacuo. The residue was triturated with a mixture of hexane and diisopropyl ether to give 3-bromo-l-(2-bromobenzyl)-2-propylindole-6-carboxamide (33 mg) as a solid.

Workup

  1. washwashed with diluted hydrochloric acid, aqueous sodium bicarbonate and brine
  2. dry with materialdried over sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue was triturated with a mixture of hexane and diisopropyl ether

Sources & evidence

ORD record
ord-ba62851ceeda4585b70b88195fb0ede9
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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