HCID 67286765, compound → HCID 67070247, compound

HRID 2390810Notes

Reaction equation

HRID 2390810 reaction equation
C([O:8][C:9]1[C:14]([C:15]2[CH:20]=[C:19]([CH:21]=[CH:22][C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=3)[C:18]([O:32][CH3:33])=[C:17]([C:34]([CH3:37])([CH3:36])[CH3:35])[CH:16]=2)=[CH:13][CH:12]=[C:11]([CH3:38])[N:10]=1)C1C=CC=CC=1>CCOC(C)=O.CO.[OH-].[OH-].[Pd+2]>[NH2:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][CH2:21][C:19]2[CH:20]=[C:15]([C:14]3[C:9](=[O:8])[NH:10][C:11]([CH3:38])=[CH:12][CH:13]=3)[CH:16]=[C:17]([C:34]([CH3:37])([CH3:36])[CH3:35])[C:18]=2[O:32][CH3:33])=[CH:24][CH:25]=1

Participants

5

Reactant 1

HCID 67286765HCID 67286765, compound

Product 1

HCID 67070247HCID 67070247, compoundYield 49.2%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

step 5—A mixture of 68 (180 mg, 0.354 mmol) and Pd(OH)2 (20 wt % on C, 75 mg, 0.107 mmol) in EtOAc (10 mL) and MeOH (10 mL) was stirred under an atmosphere of hydrogen for 2 h before the catalyst was filtered, and the filtrate was concentrated. The crude residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (75 to 100% EtOAc) to afford 68 mg (49%) of 3-{3-[2-(4-amino-phenyl)-ethyl]-5-tert-butyl-4-methoxy-phenyl}-6-methyl-1H-pyridin-2-one (70) as a foam.

Workup

  1. filtrationwas filtered
  2. concentrationthe filtrate was concentrated
  3. customThe crude residue was purified by SiO2 chromatography
  4. washeluting with an EtOAc/hexane gradient (75 to 100% EtOAc)

Sources & evidence

ORD record
ord-a94e78252fca46d3876f23ab0ad08ec1
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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