Ethyl Acetate → tert-butyl N-(7-bromo-2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-cyclopropylmethylcarbamate

HRID 2253363Notes

Reaction equation

HRID 2253363 reaction equation
[Br:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:19][CH3:20])[C:10]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[C:6]2[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:24][CH:25]1[CH2:27][CH2:26]1.C(OCC)(=O)C>CN(C)C=O>[Br:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:19][CH3:20])[C:10]([N:11]([CH2:24][CH:25]3[CH2:27][CH2:26]3)[C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 21084185tert-butyl N-(7-bromo-2-ethylpyrazolo[1,5-a]pyridin-3-yl)carbamate

Product 1

HCID 21084186tert-butyl N-(7-bromo-2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-cyclopropylmethylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl N-(7-bromo-2-ethylpyrazolo[1,5-a]pyridin-3-yl)carbamate (658 mg) in N,N-dimethylformamide (15 mL) was added sodium hydride (60% in oil; 116 mg) at room temperature under a nitrogen stream, and the reaction mixture was stirred for 30 minutes. (Bromomethyl)cyclopropane (0.286 mL) was added thereto at the same temperature, and the reaction mixture was stirred for 1 hour at 60° C. After completion of the reaction, the reaction mixture was gradually added to ice, ethyl acetate was added and the organic extract was washed with water and brine, after which it was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to afford a crude product of tert-butyl N-(7-bromo-2-ethylpyrazolo[1,5-a]pyridin-3-yl) -N-cyclopropylmethylcarbamate.

Workup

  1. stirringat the same temperature, and the reaction mixture was stirred for 1 hour at 60° C
  2. customAfter completion of the reaction
  3. additionwas added
  4. extractionthe organic extract
  5. washwas washed with water and brine
  6. dry with materialafter which it was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-861fadf9662f4f0aa3de982bdea52c35
Source dataset
uspto-grants-2008_01
Patent number
US07323569B2

Reaction notes

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