Water → 3-methanesulfonyl-1H-indazole

HRID 1500851노트

반응식

HRID 1500851 반응식
Cl[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.[CH3:11][S-:12].[Na+].[OH2:14].C1C=C(Cl)C=C(C(OO)=[O:23])C=1>CN(C=O)C.C(Cl)Cl>[CH3:11][S:12]([C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1)(=[O:23])=[O:14]

참가 물질

7

반응물 4

HCID 962Water2회HCID 70297m-Chloroperbenzoic acidHCID 958943-Chloro-1H-indazoleHCID 4378561Sodium methanethiolate

생성물 1

HCID 1785048563-methanesulfonyl-1H-indazole수율 34%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-chloro-1H-indazole (100 mg, 0.65 mmol) in DMF (2 mL) was added sodium methanethiolate (91 mg, 1.3 mmol). The resultant mixture was heated at 150° C. under microwave radiation for 1 h. After cooled to RT, 10 mL of water was added and extracted with ethyl acetate (3×30 mL). The combined organic phases were dried over anhydrous Na2SO4 and concentrated to give crude sulfide which was used for next step directly. To a solution of crude sulfide (0.4 g, 2.4 mmol) in DCM (15 mL) was added m-CPBA (0.84 g, 4.8 mmol) at RT. The mixture was stirred for 4 hrs, 20 mL of water was added. The organic phase were washed with brine and dried over anhydrous Na2SO4, evaporated in vacuum, the residue was purified by chromatography on silica gel to afford product 3-methanesulfonyl-1H-indazole (0.16 g, yield: 34%) as off-white solid, MS obsd. (ESI+) [(M+H)+] 197.1.

후처리

  1. extractionextracted with ethyl acetate (3×30 mL)
  2. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customto give crude sulfide which
  5. washThe organic phase were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated in vacuum
  8. customthe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-0aaa23733ad6483ea6383b9ec7e2d988
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206191B2

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