HCID 178418361, compound → HCID 178507138, compound

HRID 2243330Notes

Reaction equation

HRID 2243330 reaction equation
[H][H].[F:3][C:4]([F:31])([F:30])[O:5][C:6]1[CH:29]=[CH:28][C:9]2[NH:10][C:11]([C:13]3[C:25]4[C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[C:18](=[N:26]O)[C:17]=4[CH:16]=[CH:15][CH:14]=3)=[N:12][C:8]=2[CH:7]=1>C(O)C.O1CCCC1.[Ni]>[F:31][C:4]([F:3])([F:30])[O:5][C:6]1[CH:29]=[CH:28][C:9]2[NH:10][C:11]([C:13]3[C:25]4[C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[CH:18]([NH2:26])[C:17]=4[CH:16]=[CH:15][CH:14]=3)=[N:12][C:8]=2[CH:7]=1

Participants

6

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178526309HCID 178526309, compound

Product 1

HCID 178507138HCID 178507138, compoundYield 90.9%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The procedure used in Example 6 is followed. In a 111 ml autoclave, dissolve 730 mg of 4-(5-trifluoromethoxy-1H-benzimidazol-2-yl)-9H-fluoren-9-one oxime (Z,E), obtained in the previous stage, in a mixture of 25 ml of ethanol and 25 ml of tetrahydrofuran, add a spatula of Raney activated nickel and then subject to an initial hydrogen pressure of 1 bar and heat the autoclave at 600 for 4 hours. After cooling, the volume of hydrogen absorbed is 122 ml. After filtration of the catalyst over Celite, the filtrate is concentrated under reduced pressure and then taken up in dichloromethane and dried over magnesium sulphate. In this way, we obtain 640 mg of 4-(5-trifluoromethoxy-1H-benzimidazol-2-yl)-9H-fluorene-9(R,S)amine, in the form of a beige foam, which is used as it is in the following stage, with the following characteristics:

Workup

  1. additionadd a spatula of Raney
  2. temperatureheat the autoclave at 600 for 4 hours
  3. temperatureAfter cooling
  4. customthe volume of hydrogen absorbed
  5. filtrationAfter filtration of the catalyst over Celite
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-d0d32a77bbaa413eb0dc2c4fcf9f7026
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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