Pyridine → 2-Isopropyl-3-(2-methylprop-1-enyl)pyrazolo[1,5-a]pyridine

HRID 731755Notes

Reaction equation

HRID 731755 reaction equation
[CH:1]([C:4]1[C:12]([CH:13](O)[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].P(Cl)(Cl)(Cl)(Cl)Cl.N1C=CC=CC=1>C1C=CC=CC=1>[CH:1]([C:4]1[C:12]([CH:13]=[C: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

5

Reactant 3

HCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 133917031-(2-Isopropyl-pyrazolo[1,5-a]pyridin-3-yl)-2-methyl-propan-1-ol

Product 1

HCID 578374652-Isopropyl-3-(2-methylprop-1-enyl)pyrazolo[1,5-a]pyridineYield 26.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

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.

Workup

  1. customThe crude 2-isopropyl-3-(2-methylprop-1-enyl)pyrazolo[1,5-a]pyridine obtained
  2. customwas purified on an Al2O3 column

Sources & evidence

ORD record
ord-3575370fb5db45e79913d6082bdc5441
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

Loading…