Water → 3-methanesulfonyl-1H-indazole

HRID 1500851ノート

反応式

HRID 1500851 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 1785048563-methanesulfonyl-1H-indazole収率 34%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0aaa23733ad6483ea6383b9ec7e2d988
出典データセット
uspto-grants-2015_12
特許番号
US09206191B2

反応ノート

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