2-Mesitylenesulfonyl chloride → 6-iodo-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indazole

HRID 724356

반응식

HRID 724356 반응식
[I:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+].[C:17]1([CH3:29])[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:18]=1[S:25](Cl)(=[O:27])=[O:26]>C1COCC1>[I:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[S:25]([C:18]2[C:19]([CH3:24])=[CH:20][C:21]([CH3:23])=[CH:22][C:17]=2[CH3:29])(=[O:27])=[O:26])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 130462-Mesitylenesulfonyl chlorideHCID 129912416-iodo-1H-indazoleHCID 23676156Sodium t-butoxide

생성물 1

HCID 218773966-iodo-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indazole수율 100%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
23 °C

실험 절차

To a solution of 6-iodo-1H-indazole (7.35 g, 30.1 mmol, 1 equiv) in THF (100 mL) cooled to 0° C. under argon, was added sodium t-butoxide (2.89 g, 30.1 mmol, 1 equiv). A color change from orange to red was observed. Mesitylenesulfonyl chloride (6.60 g, 30.1 mmol, 1 equiv) was added in one portion and the ice bath was removed allowing the reaction mixture to warm to 23° C. After 40 min the mixture was quenched with saturated ammonium chloride and partitioned between water and ethyl acetate. The aqueous was extracted a total of 3 times with ethyl acetate. The combined organic material was washed with brine, dried over sodium sulfate and concentrated under reduced pressure to give 6-iodo-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indazole as an orange solid (12.8 g, 100% yield, 2:1 mixture). 1H NMR (CDCl3) 8.51 (s, 1H), 7.95 (s, 0.66H, major isomer), 7.91 (s, 0.33H, minor isomer), 7.47 (d, 0.33H, J=8.4 Hz), 7.29 (d, 0.33H, J=8.4 Hz), 7.26 (d, 0.66H, J=8.9 Hz), 7.18 (d, 0.66H, 8.9 Hz), 6.84 (s, 2H), 2.51 (s, 6H), 2.15 (s, 3H).

후처리

  1. customthe ice bath was removed
  2. customAfter 40 min the mixture was quenched with saturated ammonium chloride
  3. custompartitioned between water and ethyl acetate
  4. extractionThe aqueous was extracted a total of 3 times with ethyl acetate
  5. washThe combined organic material was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-153a6a18c8654f528761d9f9e022dbcb
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141587B2

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