4-Toluenesulfonyl chloride → 3-iodo-5-(6-isopropoxypyrazin-2-yl)-1-tosyl-1H-indole

HRID 1529310노트

반응식

HRID 1529310 반응식
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[CH:16]=[N:15][CH:14]=[C:13]([O:17][CH:18]([CH3:20])[CH3:19])[N:12]=3)[CH:9]=2)[NH:4][CH:3]=1.[H-].[Na+].[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>CN(C=O)C>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[CH:16]=[N:15][CH:14]=[C:13]([O:17][CH:18]([CH3:20])[CH3:19])[N:12]=3)[CH:9]=2)[N:4]([S:29]([C:26]2[CH:27]=[CH:28][C:23]([CH3:33])=[CH:24][CH:25]=2)(=[O:31])=[O:30])[CH:3]=1

참가 물질

5

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 679599583-iodo-5-(6-isopropoxypyrazin-2-yl)-1H-indole

생성물 1

HCID 679596923-iodo-5-(6-isopropoxypyrazin-2-yl)-1-tosyl-1H-indole수율 55%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-iodo-5-(6-isopropoxy-pyrazin-2-yl)-1H-indole (20 g, 0.053 mol) in DMF (200 mL) was added NaH (6.5 g, 0.158 mol) slowly at 0° C., and then stirred for 15 min. p-Toluenesulfonyl chloride (15.10 g, 0.079 mol) was added slowly to the reaction mixture and stirred for 1 h. The resulting mixture was poured into ice with stirring and the precipitate was formed. The resulting precipitate was collected by filtration, washed with water and dried under vacuum to give the crude product. The crude product was purified by column chromatography eluting with EtOAc and n-hexane to afford the desire 3-iodo-5-(6-isopropoxypyrazin-2-yl)-1-tosyl-1H-indole (15.5 g, 55%) as pale brown solid. MS (ESI, m/z): 533.6 (M+1).

후처리

  1. additionwas added slowly to the reaction mixture
  2. additionThe resulting mixture was poured into ice
  3. stirringwith stirring
  4. customthe precipitate was formed
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water
  7. customdried under vacuum
  8. customto give the crude product
  9. customThe crude product was purified by column chromatography
  10. washeluting with EtOAc and n-hexane

출처 및 근거

ORD 기록
ord-964dc23de72d4de3842a13df28742727
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090593B2

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