Sodium Iodide → 2-(Benzylamino)-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one

HRID 731756Notes

Reaction equation

HRID 731756 reaction equation
Cl[CH:2]([CH3:17])[C:3]([C:5]1[C:6]([CH:14]([CH3:16])[CH3:15])=[N:7][N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=12)=[O:4].[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Na+].[I-]>CO>[CH2:18]([NH:25][CH:2]([CH3:17])[C:3]([C:5]1[C:6]([CH:14]([CH3:16])[CH3:15])=[N:7][N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=12)=[O:4])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 7504BenzylamineHCID 215857512-Chloro-1-[2-(1-methylethyl)pyrazolo[1,5-a]pyridin-3-yl]-1-propanone

Product 1

HCID 578375092-(Benzylamino)-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 2.51 g of 2-chloro-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one and 2.25 ml of benzylamine in 20 ml of MeOH was added 10 mg of NaI and the solution was refluxed for 4 hours, then stirred at RT overnight. Crude 2-(benzylamino)-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one was purified on an Al2O3 column to yield 2.51 g of pure compound. Compound 1071.

Workup

  1. temperaturethe solution was refluxed for 4 hours
  2. customCrude 2-(benzylamino)-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one was purified on an Al2O3 column

Sources & evidence

ORD record
ord-623d282385f847a793bf8a902b5037f9
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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