Cornforth reagent → HCID 58073906, compound

HRID 1470667Notes

Reaction equation

HRID 1470667 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([C:14]3[C:19]([F:20])=[C:18]([F:21])[C:17]([C:22]4[CH:27]=[CH:26][C:25]([CH2:28][OH:29])=[CH:24][CH:23]=4)=[C:16]([F:30])[C:15]=3[F:31])[NH:10][C:9]=2[CH:8]=[C:7]([CH3:32])[CH:6]=1)=[O:4].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([C:14]3[C:15]([F:31])=[C:16]([F:30])[C:17]([C:22]4[CH:23]=[CH:24][C:25]([CH:28]=[O:29])=[CH:26][CH:27]=4)=[C:18]([F:21])[C:19]=3[F:20])[NH:10][C:9]=2[CH:8]=[C:7]([CH3:32])[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 58073896HCID 58073896, compound

Product 1

HCID 58073906HCID 58073906, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-methyl-2-(2,3,5,6-tetrafluoro-4′-hydroxymethyl-biphenyl-4-yl)-1H-benzoimidazole-4-carboxylic acid methyl ester (0.55 g, 1.22 mmol) in dry tetrahydrofuran (50 mL) was added pyridinium dichromate (0.2 g) portion wise. The reaction mixture was stirred at room temperature in nitrogen atmosphere for 14 hours. TLC shows completion of the reaction. The reaction mixture was filtered over celite bed and the filtrate was concentrated to dryness. The resulting residue was purified by column chromatography using 20% ethyl acetate in hexane to get to get the title compound as colorless solid (0.4 g, 74.07%).

Workup

  1. customcompletion of the reaction
  2. filtrationThe reaction mixture was filtered over celite bed
  3. concentrationthe filtrate was concentrated to dryness
  4. customThe resulting residue was purified by column chromatography
  5. customto get

Sources & evidence

ORD record
ord-f6d10040ddb94956a57ca41aeb823e7f
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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