HCID 22627483, compound → HCID 18784032, compound

HRID 1108745Notes

Reaction equation

HRID 1108745 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-1-(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-e92db28c53f3409891be2b0751017622
Source dataset
uspto-grants-2000_05
Patent number
US06069156

Reaction notes

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