N-bromobutanimide → Methyl 6-((4-bromophenyl)amino)-7-fluoro-1H-benzo[d]imidazole-5-carboxylate

HRID 2104002Notes

Reaction equation

HRID 2104002 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:12]([F:21])[C:8]2[N:9]=[CH:10][NH:11][C:7]=2[CH:6]=1)=[O:4].[Br:22]N1C(=O)CCC1=O>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[C:13]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([Br:22])=[CH:19][CH:20]=2)=[C:12]([F:21])[C:8]2[N:9]=[CH:10][NH:11][C:7]=2[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 11818480Methyl 7-fluoro-6-(phenylamino)-1H-benzo[d]imidazole-5-carboxylate

Product 1

HCID 66885552Methyl 6-((4-bromophenyl)amino)-7-fluoro-1H-benzo[d]imidazole-5-carboxylateYield 100.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Fluoro-6-phenylamino-3H-benzoimidazole-5-carboxylic acid methyl ester 27a (4.99 g, 17.51 mmol) is dissolved in N,N-dimethylformamide (275 mL). N-bromosuccinimide (3.15 g, 17.70 mmol) is added as a solid and the reaction mixture is stirred at room temperature under N2. After 30 minutes, the reaction mixture is quenched by the addition of aqueous saturated sodium bisulfite solution. The reaction mixture is then poured into a separatory funnel, diluted with water and ethyl acetate and the layers separated. The aqueous layer is extracted with ethyl acetate. The combined organic extracts are washed three times with water, once with brine and then are dried (Na2SO4) and concentrated under reduced pressure to yield 6.38 g (100%) of the pure desired product as a tan solid. MS ESI (+) m/z 364, 366 (M+ Br pattern) detected.

Workup

  1. customthe reaction mixture is quenched by the addition of aqueous saturated sodium bisulfite solution
  2. additionThe reaction mixture is then poured into a separatory funnel
  3. additiondiluted with water and ethyl acetate
  4. customthe layers separated
  5. extractionThe aqueous layer is extracted with ethyl acetate
  6. washThe combined organic extracts are washed three times with water
  7. dry with materialonce with brine and then are dried (Na2SO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-176917062fd940bdab2dc3c336febdb9
Source dataset
uspto-grants-2009_08
Patent number
US07576114B2

Reaction notes

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