HCID 67069886, compound → HCID 67070050, compound

HRID 2390806Notes

Reaction equation

HRID 2390806 reaction equation
C([O:8][C:9]1[C:14]([CH:15]=[CH:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=2)=[CH:13][C:12]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:11][C:10]=1[C:30]1[C:31]([O:36][CH3:37])=[N:32][CH:33]=[CH:34][CH:35]=1)C1C=CC=CC=1>CCOC(C)=O.CO.[OH-].[OH-].[Pd+2]>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][CH2:15][C:14]2[CH:13]=[C:12]([C:26]([CH3:29])([CH3:27])[CH3:28])[CH:11]=[C:10]([C:30]3[C:31]([O:36][CH3:37])=[N:32][CH:33]=[CH:34][CH:35]=3)[C:9]=2[OH:8])=[CH:18][CH:19]=1

Participants

5

Reactant 1

HCID 67069886HCID 67069886, compound

Product 1

HCID 67070050HCID 67070050, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

step 4—A mixture of 52 (311 mg, 0.630 mmol) and Pd(OH)2 (20% wt. on carbon, 103 mg, 0.146 mmol) in EtOAc (10 mL) and MeOH (10 mL) was stirred under a H2 atmosphere overnight. The catalyst was filtered, and the filtrate was concentrated. The crude residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (10 to 25% EtOAc) to afford 156 mg (66%) of 2-[2-(4-amino-phenyl)-ethyl]-4-tert-butyl-6-(2-methoxy-pyridin-3-yl)-phenol (54) as a colorless oil.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe crude residue was purified by SiO2 chromatography
  4. washeluting with an EtOAc/hexane gradient (10 to 25% EtOAc)

Sources & evidence

ORD record
ord-8cc97c2c92b54afb8199c9e26a50bb88
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

Loading…