HCID 58148151, compound → HCID 136184233, compound

HRID 884906Notes

Reaction equation

HRID 884906 reaction equation
C([O:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[C:15]1[O:16][C:17]2[CH:23]=[CH:22][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:20][C:18]=2[N:19]=1)C1C=CC=CC=1.[H][H]>[Pd].C(O)(=O)C>[C:24]([C:21]1[CH:22]=[CH:23][C:17]2[O:16][C:15]([C:14]3[CH:13]=[CH:12][N:11]=[CH:10][C:9]=3[OH:8])=[N:19][C:18]=2[CH:20]=1)([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 2

HCID 58148151HCID 58148151, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 136184233HCID 136184233, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2.1 g of 2-(3-benzyloxypyridin-4-yl)-5-tert-butylbenzoxazole, 0.58 g of 5% palladium on carbon and 50 ml of acetic acid was stirred under about one atmosphere of hydrogen at room temperature for six hours. The reaction mixture was filtered through Celite™. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.3 g of 4-(5-tert-butylbenzoxazole-2-yl)pyridin-3-ol (hereinafter, referred to as “active compound 103”).

Workup

  1. filtrationThe reaction mixture was filtered through Celite™
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5c60fb0fcbff4135ba4af16c45121386
Source dataset
uspto-grants-2012_08
Patent number
US08242133B2

Reaction notes

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