HCID 12301740, compound → Pyrazolo[1,5-a]pyridine-2-acetic acid, 4,5,6,7-tetrahydro-3-(methoxycarbonyl)-, methyl ester

HRID 1913439Notes

Reaction equation

HRID 1913439 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][N:7]2[N:6]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:8]2[CH2:9][CH2:10][CH2:11][CH2:12][N:7]2[N:6]=1

Participants

4

Reactant 1

HCID 12301740HCID 12301740, compound

Product 1

HCID 67406521Pyrazolo[1,5-a]pyridine-2-acetic acid, 4,5,6,7-tetrahydro-3-(methoxycarbonyl)-, methyl esterYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 2-(2-methoxy-2-oxoethyl)pyrazolo[1,5-a]pyridine-3-carboxylate (42.0 mg, 0.17 mmol), as prepared according to the procedure described in Stefan Löber, S.; Hübner, H.; Gmeiner B.; Biorg. Med. Chem. Lett. 12(17), 2377 (2002), was dissolved in MeOH (5 mL) and was hydrogenated on an H-Cube® hydrogenation apparatus with 10% Pd/C at 40° C. for 1 hour. The methanol solution was removed in vacuo to afford methyl 2-(2-methoxy-2-oxoethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-3-carboxylate (39 mg, 91%), which was used directly in the next step without further purification.

Workup

  1. customThe methanol solution was removed in vacuo

Sources & evidence

ORD record
ord-116999b4b15049329616eafd7105455a
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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