Potassium Carbonate → HCID 59682310, compound

HRID 1714228Notes

Reaction equation

HRID 1714228 reaction equation
[Cl:1][C:2]1[C:15]([Cl:16])=[CH:14][C:5]2[NH:6][C:7]([CH2:9][C:10]([F:13])([F:12])[F:11])=[N:8][C:4]=2[CH:3]=1.[C:17](=[O:20])([O-])[O-].[K+].[K+].CO[C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([N+:33]([O-:35])=[O:34])[CH:32]=1)[CH2:28]Br>CN(C=O)C>[Cl:16][C:15]1[C:2]([Cl:1])=[CH:3][C:4]2[N:8]([CH2:28][C:27]3[CH:30]=[C:31]([N+:33]([O-:35])=[O:34])[CH:32]=[CH:25][C:26]=3[O:20][CH3:17])[C:7]([CH2:9][C:10]([F:12])([F:13])[F:11])=[N:6][C:5]=2[CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 116519105,6-dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzimidazoleHCID 18361097HCID 18361097, compound

Product 1

HCID 59682310HCID 59682310, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5,6-dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzimidazole (387 mg) in DMF (5 mL) was added potassium carbonate powder (596 mg) and 3-methoxy-5-nitro-benzyl bromide (1.06 g). The resulting mixture was stirred at room temperature overnight. The reaction mixture was quenched with water, extracted with EtOAc, and dried over Na2SO4. The crude product was purified by silica gel chromatography (10%-40% EtOAc/hexanes) to yield the title compound as a peach-colored solid.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. customThe crude product was purified by silica gel chromatography (10%-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-177852fb48ee4b7286525dd8d5d56c1d
Source dataset
uspto-grants-2010_09
Patent number
US07795446B2

Reaction notes

Loading…