Water → 3-methanesulfonyl-1H-indazole

HRID 1500851Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1500851
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]

Komponenten

7

Edukt 4

HCID 962Water2×HCID 70297m-Chloroperbenzoic acidHCID 958943-Chloro-1H-indazoleHCID 4378561Sodium methanethiolate

Produkt 1

HCID 1785048563-methanesulfonyl-1H-indazoleAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-0aaa23733ad6483ea6383b9ec7e2d988
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206191B2

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