Diisopropyl Ether → HCID 178507134, compound

HRID 2243326Notes

Reaction equation

HRID 2243326 reaction equation
[H][H].C(OC(C)C)(C)C.[F:10][C:11]1[CH:34]=[C:33]([F:35])[C:14]2[NH:15][C:16]([C:18]3[C:30]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[C:23](=[N:31]O)[C:22]=4[CH:21]=[CH:20][CH:19]=3)=[N:17][C:13]=2[CH:12]=1>C(O)C.O1CCCC1.[Ni]>[F:10][C:11]1[CH:34]=[C:33]([F:35])[C:14]2[NH:15][C:16]([C:18]3[C:30]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[CH:23]([NH2:31])[C:22]=4[CH:21]=[CH:20][CH:19]=3)=[N:17][C:13]=2[CH:12]=1

Participants

7

Reactant 3

HCID 7914Diisopropyl EtherHCID 178418361HCID 178418361, compoundHCID 178526305HCID 178526305, compound

Product 1

HCID 178507134HCID 178507134, compoundYield 74.3%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The procedure used in Example 6 is followed. In a 211 ml autoclave, dissolve 1.85 g of 4-(5,7-difluoro-1H-benzimidazol-2-yl)-9H-fluoren-9-one oxime (Z,E), obtained in the previous stage, in a mixture of 70 ml of ethanol and 70 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 60° for 6 hours. After cooling, the volume of hydrogen absorbed is 342 ml. After filtration of the catalyst, the filtrate is concentrated under reduced pressure and then taken up in a mixture of dichloromethane with a small amount of methanol and dried over magnesium sulphate, and the crude solid obtained is made into a paste with diisopropyl ether. In this way, we obtain 1.32 g of 4-(5,7-difluoro-1H-benzimidazol-2-yl)-9H-fluorene-9(R,S)-amine, in the form of a grey powder, 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 60° for 6 hours
  3. temperatureAfter cooling
  4. customthe volume of hydrogen absorbed
  5. filtrationAfter filtration of the catalyst
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. additiontaken up in a mixture of dichloromethane with a small amount of methanol
  8. dry with materialdried over magnesium sulphate
  9. customthe crude solid obtained

Sources & evidence

ORD record
ord-6537297ef31c45d1954c1b167a704b9b
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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