1,4-Cyclohexadiene → HCID 71074017, compound

HRID 340805Notes

Reaction equation

HRID 340805 reaction equation
C1(C2C=CC=CC=2)C=CC(C[N:8]2[C:12]3[CH:13]=[C:14]([F:30])[C:15]([C:18]4[CH:19]=[C:20]5[C:24](=[CH:25][CH:26]=4)[N:23]([CH:27]4[CH2:29][CH2:28]4)[CH:22]=[CH:21]5)=[C:16]([F:17])[C:11]=3[N:10]=[C:9]2[O:31][CH:32]2[CH2:37][CH2:36][CH:35]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:34][CH2:33]2)=CC=1.C1CC=CCC=1>CCOC(C)=O.CCO.[OH-].[OH-].[Pd+2]>[CH:27]1([N:23]2[C:24]3[C:20](=[CH:19][C:18]([C:15]4[C:14]([F:30])=[CH:13][C:12]5[NH:8][C:9]([O:31][CH:32]6[CH2:33][CH2:34][CH:35]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:36][CH2:37]6)=[N:10][C:11]=5[C:16]=4[F:17])=[CH:26][CH:25]=3)[CH:21]=[CH:22]2)[CH2:29][CH2:28]1

Participants

6

Reactant 2

HCID 123431,4-CyclohexadieneHCID 67408688HCID 67408688, compound

Product 1

HCID 71074017HCID 71074017, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 4-{[1-(biphenyl-4-ylmethyl)-5-(1-cyclopropyl-1H-indol-5-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclohexane-carboxylate (0.080 g, 0.124 mmol) and Pd(OH)2 (0.023 g, 0.032 mmol) in 1.65 mL of EtOAc and 0.83 mL of EtOH was added 1,4-cyclohexadiene (0.300 mL, 3.19 mmol). The resulting black suspension was microwaved at 130° C. for 2 h, then filtered through a Celite™ pad, and washed with 100% EtOAc. The resulting filtrate was concentrated in vacuo. Purification of the resulting crude residue by preparative TLC (40% EtOAc/hexanes) afforded the title compound. LCMS: calculated for C27H27F2N3O3 479.52, observed m/e 480.1 (M+11)+ (Rt 2.58/4 min).

Workup

  1. customThe resulting black suspension was microwaved at 130° C. for 2 h
  2. filtrationfiltered through a Celite™ pad
  3. washwashed with 100% EtOAc
  4. concentrationThe resulting filtrate was concentrated in vacuo
  5. customPurification of the resulting crude residue by preparative TLC (40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-fe5c2a72e263400aac4b9c1a01537646
Source dataset
uspto-grants-2014_11
Patent number
US08895596B2

Reaction notes

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