N-Bromosuccinamide → HCID 69019219, compound

HRID 1865115Notes

Reaction equation

HRID 1865115 reaction equation
[N].N1C=CC=C1.[C:7]([C:9]1[C:10]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[S:27][CH:28]=[CH:29][C:30]=3[N+:31]([O-:33])=[O:32])=[CH:22][CH:21]=2)=[C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:12]([CH3:14])[CH:13]=1)#[N:8].[Br:34]NC(=O)CCC(N)=O>C(Cl)Cl>[Br:34][C:13]1[N:12]([CH3:14])[C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:10]([C:20]2[CH:21]=[CH:22][C:23]([C:26]3[S:27][CH:28]=[CH:29][C:30]=3[N+:31]([O-:33])=[O:32])=[CH:24][CH:25]=2)[C:9]=1[C:7]#[N:8]

Participants

5

Reactant 3

HCID 9834204N-BromosuccinamideHCID 69022964HCID 69022964, compoundHCID 178507910HCID 178507910, compound

Product 1

HCID 69019219HCID 69019219, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound is prepared in a manner analogous to the procedure set forth in Scheme XXIII, step A wherein the starting pyrrole nitrogen is already methylated. For example, to a solution of ethyl 4-cyano-1-methyl-3-[4-(3-nitro(2-thienyl))phenyl]pyrrole-2-carboxylate, prepared directly above (1.0 mmol) in methylene chloride in an ice bath add N-bromo-succinamide (1.5 mmol). Allow the reaction to warm to room temperature and stir for 18 hours. After this time, wash reaction with water while extracting with ethyl acetate. Dry organic layer with sodium sulfate, filter and concentrate in vacuo to provide the title compound. Use as crude in the next step.

Workup

  1. customThe title compound is prepared in a manner analogous to the procedure
  2. customthe reaction
  3. washAfter this time, wash
  4. customreaction with water
  5. extractionwhile extracting with ethyl acetate
  6. filtrationDry organic layer with sodium sulfate, filter
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-6bdc32b9fead437ca4bed8117861d9df
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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