Ibudilast → 1-(2-Isopropyl-pyrazolo[1,5-a]pyridin-3-yl)-2-methyl-propan-1-ol

HRID 731754Notes

Reaction equation

HRID 731754 reaction equation
[CH:1]([C:4]1[C:12]([C:13](=[O:17])[CH:14]([CH3:16])[CH3:15])=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[CH:1]([C:4]1[C:12]([CH:13]([OH:17])[CH:14]([CH3:16])[CH3:15])=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 3671IbudilastHCID 4311764Sodium borohydride

Product 1

HCID 133917031-(2-Isopropyl-pyrazolo[1,5-a]pyridin-3-yl)-2-methyl-propan-1-olYield 110.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 9.2 g of 1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one in 25 ml of MeOH was added 1.5 g of NaBH4. The solution was stirred at RT overnight. 10.25 g of oily 1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-ol was obtained after workup. 1.05 g of 1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-ol in 10 ml of benzene was treated with 0.92 g of PCl5 and 1 ml of pyridine with stirring for 3 hours at RT. The crude 2-isopropyl-3-(2-methylprop-1-enyl)pyrazolo[1,5-a]pyridine obtained was purified on an Al2O3 column to furnish 255 mg of pure compound. Compound 1049.

Sources & evidence

ORD record
ord-37f8500c6c394daba045fe57e2180bb0
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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