2,6-Dichlorobenzaldehyde → 2-(2,6-dichlorophenyl)-6,7-difluoro-3H-benzoimidazole-5-carboxylic acid methyl ester

HRID 1514908Notes

Reaction equation

HRID 1514908 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([NH2:11])=[C:6]([F:12])[C:5]=1[F:13].[Cl:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:17]=1[CH:18]=O.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3]>CS(C)=O>[CH3:1][O:2][C:3]([C:4]1[C:5]([F:13])=[C:6]([F:12])[C:7]2[N:11]=[C:18]([C:17]3[C:16]([Cl:15])=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:24])[NH:10][C:8]=2[CH:9]=1)=[O:14]

Participants

5

Reactant 3

HCID 67372,6-DichlorobenzaldehydeHCID 2733225Ytterbium triflateHCID 86651263Methyl 4,5-diamino-2,3-difluorobenzoate

Product 1

HCID 669660542-(2,6-dichlorophenyl)-6,7-difluoro-3H-benzoimidazole-5-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 4,5-diamino-2,3-difluorobenzoic acid methyl ester (404 mg, 2.0 mmol) and 2,6-dichlorobenzaldehyde in DMSO (15 mL) was added Yb(OTf)3 (248 mg, 20%) and the solution was stirred at ambient temperature overnight. The reaction was quenched with water and the aqueous layer was extracted with EtOAc. The organic layer was washed with water, brine, dried with MgSO4, and filtered. The solvent was removed under reduced pressure to give 2-(2,6-dichlorophenyl)-6,7-difluoro-3H-benzoimidazole-5-carboxylic acid methyl ester as a yellow solid.

Workup

  1. customThe reaction was quenched with water
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-79b86897f56b4880837fc9544b65f46d
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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