Ethyl Acetate → tert-butyl N-cyclopropylmethyl-N-[7-iodo-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate

HRID 2253380Notes

Reaction equation

HRID 2253380 reaction equation
[I:1][C:2]1[N:7]2[N:8]=[C:9]([S: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>[CH:25]1([CH2:24][N:11]([C:10]2[C:9]([S:19][CH3:20])=[N:8][N:7]3[C:2]([I:1])=[CH:3][CH:4]=[CH:5][C:6]=23)[C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:17])[CH3:15])[CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 21984511tert-Butyl N-[7-iodo-2-methylthiopyrazolo[1,5-a]pyridin-3-yl]carbamate

Product 1

HCID 21084196tert-butyl N-cyclopropylmethyl-N-[7-iodo-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl N-[7-iodo-2-methylthiopyrazolo[1,5-a]pyridin-3-yl]carbamate (600 mg) in N,N-dimethylformamide (6 mL) was added sodium hydride (60% in oil; 80 mg) with ice bath, and the reaction mixture was stirred for 30 minutes at room temperature. (Bromomethyl)cyclopropane (0.22 mL) was added to the reaction mixture at the same temperature, and stirring was continued for 1 hour at 40° C. After completion of the reaction, the reaction mixture was gradually added to ice, extraction was performed with ethyl acetate, and the organic extract was washed with water and brine. The organic extract was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to afford a crude product of tert-butyl N-cyclopropylmethyl-N-[7-iodo-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate.

Workup

  1. stirringstirring
  2. waitwas continued for 1 hour at 40° C
  3. customAfter completion of the reaction
  4. additionthe reaction mixture was gradually added to ice, extraction
  5. extractionthe organic extract
  6. washwas washed with water and brine
  7. extractionThe organic extract
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-29b47fb0a31342abbaeea5bc233050a5
Source dataset
uspto-grants-2008_01
Patent number
US07323569B2

Reaction notes

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