Acetic Acid → Diisopropyl Ether

HRID 2243345Notes

Reaction equation

HRID 2243345 reaction equation
[F:1][C:2]1[C:25]([F:26])=[CH:24][C:5]2[NH:6][C:7]([C:9]3[C:21]4[C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14](=[N:22]O)[C:13]=4[CH:12]=[CH:11][CH:10]=3)=[N:8][C:4]=2[CH:3]=1.[C:27]([OH:30])(=O)[CH3:28].[CH2:31](O)C>O.[Zn]>[CH:27]([O:30][CH:25]([CH3:24])[CH3:2])([CH3:28])[CH3:31].[F:26][C:25]1[C:2]([F:1])=[CH:3][C:4]2[NH:8][C:7]([C:9]3[C:21]4[C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[CH:14]([NH2:22])[C:13]=4[CH:12]=[CH:11][CH:10]=3)=[N:6][C:5]=2[CH:24]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 702EthanolHCID 137227840HCID 137227840, compound

Product 2

HCID 7914Diisopropyl EtherHCID 67358643HCID 67358643, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

The procedure used in Example 216 is followed. In a 100 ml round-bottomed flask under an argon atmosphere, dissolve 830 mg of 4-(5,6-difluoro-1H-benzimidazol-2-yl)-9H-fluoren-9-one oxime (Z,E), obtained in the previous stage, in a mixture of 5.5 ml of ethanol and 5.5 ml of water and 5.5 ml of acetic acid, at room temperature, add 624 mg of zinc in three stages, and, between each addition, stir for approximately one hour to two hours. Add Celite and filter. The filtrate is concentrated under pressure. The crude product is purified by flash chromatography on silica gel (40-63 μm), eluting with a mixture of dichloromethane and ammonia as a 7N solution in methanol (98/2 by volume). After formation of a paste with diisopropyl ether, in this way we obtain 653 mg of 4-(5,6-difluoro-1H-benzimidazol-2-yl)-9H-fluorene-9(R,S)-amine, in the form of a white powder, which is used as it is in the following stage, with the following characteristics:

Workup

  1. additionbetween each addition
  2. filtrationAdd Celite and filter
  3. concentrationThe filtrate is concentrated under pressure
  4. customThe crude product is purified by flash chromatography on silica gel (40-63 μm)
  5. washeluting with a mixture of dichloromethane and ammonia as a 7N solution in methanol (98/2 by volume)

Sources & evidence

ORD record
ord-71711611570a446f9308e668d285605e
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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