1,1-Dimethylethyl 4'-[(2-butyl pyrazolo (1,5-a)pyridin-3-yl)methyl]-(1,1-biphenyl) 2-carboxylate → 1,1-Dimethylethyl 4'-[(2-butyl 4,5,6,7-tetrahydro pyrazolo(1,5-a)pyridin-3-yl)methyl](1,1'-biphenyl)2-carboxylate

HRID 37209Notes

Reaction equation

HRID 37209 reaction equation
[CH2:1]([C:5]1[C:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[C:22]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:17][CH:16]=2)=[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][N:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4]>[Pt](=O)=O.C(O)(=O)C>[CH2:1]([C:5]1[C:13]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[C:22]([C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:19][CH:20]=2)=[C:8]2[CH2:9][CH2:10][CH2:11][CH2:12][N:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 190324701,1-Dimethylethyl 4'-[(2-butyl pyrazolo (1,5-a)pyridin-3-yl)methyl]-(1,1-biphenyl) 2-carboxylate

Product 1

HCID 190324691,1-Dimethylethyl 4'-[(2-butyl 4,5,6,7-tetrahydro pyrazolo(1,5-a)pyridin-3-yl)methyl](1,1'-biphenyl)2-carboxylateYield 0.1%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

220 g of the product of Example 6, 20 ml of acetic acid and 100 mg of 82% platinum dioxide. Filtration was carried out followed by extraction with ethyl acetate. The extracts were purified by chromatography on silica (essence G: 80/ethyl acetate: 20) to obtain 145 mg of the expected product.

Workup

  1. filtrationFiltration
  2. extractionwas carried out followed by extraction with ethyl acetate
  3. customThe extracts were purified by chromatography on silica (essence G: 80/ethyl acetate: 20)

Sources & evidence

ORD record
ord-b1b1c15c5b8d418e87b33fd39667395c
Source dataset
uspto-grants-1995_05
Patent number
US05420138

Reaction notes

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