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

HRID 1749199Notes

Reaction equation

HRID 1749199 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 (4.99 g, 17.51 mmol) was dissolved in N,N-dimethylformamide (275 ml). N-bromosuccinimide (3.15 g, 17.70 mmol) was added as a solid and the reaction mixture was stirred at room temperature under N2. After 30 minutes, the reaction mixture was quenched by the addition of aqueous saturated sodium bisulfite solution. The reaction mixture was then poured into a separatory funnel, diluted with water and ethyl acetate and the layers separated. The aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed three times with water, once with brine and then 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 was quenched by the addition of aqueous saturated sodium bisulfite solution
  2. additionThe reaction mixture was then poured into a separatory funnel
  3. additiondiluted with water and ethyl acetate
  4. customthe layers separated
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic extracts were washed three times with water
  7. dry with materialonce with brine and then dried (Na2SO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ca520823b9fb4d9cb04904c4548cfb00
Source dataset
uspto-grants-2015_10
Patent number
US09156795B2

Reaction notes

Loading…