1,4-Cyclohexadiene → HCID 67442362, compound

HRID 340789Notes

Reaction equation

HRID 340789 reaction equation
[C:1]1([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:39]([F:40])=[CH:38][C:10]3[N:11](CC4C=CC(C5C=CC=CC=5)=CC=4)[C:12]([O:14][CH:15]4[CH2:20][CH2:19][CH2:18][CH:17]([C:21]([O:23][CH3:24])=[O:22])[CH2:16]4)=[N:13][C:9]=3[C:8]=2[F:41])=[CH:3][CH:2]=1.C1CC=CCC=1>[OH-].[OH-].[Pd+2].CCOC(C)=O.CCO>[C:1]1([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH:2]=[CH:3][C:4]([C:7]2[C:39]([F:40])=[CH:38][C:10]3[NH:11][C:12]([O:14][CH:15]4[CH2:20][CH2:19][CH2:18][CH:17]([C:21]([O:23][CH3:24])=[O:22])[CH2:16]4)=[N:13][C:9]=3[C:8]=2[F:41])=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 123431,4-CyclohexadieneHCID 67407131HCID 67407131, compound

Product 1

HCID 67442362HCID 67442362, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of methyl 3-{[5-(biphenyl-4-yl)-1-(biphenyl-4-ylmethyl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclohexanecarboxylate (0.080 g, 0.127 mmol) and Pearlman's Catalyst (0.016 g, 0.023 mmol) in EtOAc (1.5 ml) and EtOH (0.75 ml) was treated with 1,4-cyclohexadiene (0.24 ml, 2.56 mmol). The resulting reaction mixture was microwaved at 120° C. for 90 minutes and then cooled. The cooled reaction mixture was filtered through a Celite™ pad and the filtrate was removed in vacuo. Purification of the resulting residue by reverse phase HPLC eluting with 50-100% MeCN/H2O afforded the title compound as a white solid. LC-MS: calculated for C27H24F2N2O3 462.18, observed m/e: 463.01.01 (M+H)+ (Rt 2.31/4 min).

Workup

  1. customThe resulting reaction mixture
  2. customwas microwaved at 120° C. for 90 minutes
  3. temperaturecooled
  4. customThe cooled reaction mixture
  5. filtrationwas filtered through a Celite™ pad
  6. customthe filtrate was removed in vacuo
  7. customPurification of the resulting residue by reverse phase HPLC
  8. washeluting with 50-100% MeCN/H2O

Sources & evidence

ORD record
ord-a138e05650ba494b85c5a46f6db5ac39
Source dataset
uspto-grants-2014_11
Patent number
US08895596B2

Reaction notes

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