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

HRID 347846노트

반응식

HRID 347846 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-382d39dfb6b6467aa08ed6438b8c9833
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176216B2

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