Hydrochloric Acid → Ethyl 2-(1-(methylsulphonyl)indolin-5-yl)propanoate

HRID 2194929

反応式

HRID 2194929 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([CH3:14])(=[O:13])=[O:12])[CH2:6][CH2:5]2.[CH2:15]([O:17][C:18](=[O:22])[CH:19](Cl)[CH3:20])[CH3:16].C(O)(C(F)(F)F)=O.Cl>CN(C=O)C.[Mn].[Ni](Br)Br.N1C=CC=CC=1C1C=CC=CN=1>[CH3:14][S:11]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([CH:19]([CH3:20])[C:18]([O:17][CH2:15][CH3:16])=[O:22])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1)(=[O:13])=[O:12]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 10807Ethyl 2-chloropropionateHCID 5759865-Bromo-1-(methylsulfonyl)indoline

生成物 1

HCID 58093552Ethyl 2-(1-(methylsulphonyl)indolin-5-yl)propanoate収率 14%

試薬・触媒・溶媒 3

HCID 23930Manganese触媒HCID 10883287(2,2'-Bipyridine)nickel(II) dibromide触媒HCID 6228Dimethylformamide溶媒

実験手順

5-bromo-1-(methylsulphonyl)indoline (13.4 mmol, 3.7 g) and ethyl-2-chloropropionate (17.4 mmol, 2.38 g) were dissolved in DMF (7 ml) in a protective gas atmosphere at room temperature. Subsequently, manganese (26.8 mmol, 1.47 g), (2,2′-bipyridine) nickel(II)-dibromide (0.938 mmol, 0.351 g) and TFA (0.348 mmol, 27 μl) were added and stirring was carried out at 50° C. for 1.5 h. After cooling the reaction mixture to room temperature, hydrolysis was carried out at room temperature with 1 N HCl (25 ml) and the mixture was extracted with diethyl ether (3×25 ml). The combined organic phases were washed with water (25 ml) and aq. sat. NaCl solution (25 ml) and dried over magnesium sulphate. After removing the solvent in a vacuum and purifying the residue by column chromatography (SiO2, diethyl ether/hexane=3:1), 0.558 g (14% yield) of ethyl 2-(1-(methylsulphonyl)indolin-5-yl)propanoate were obtained.

後処理

  1. customhydrolysis
  2. extractionthe mixture was extracted with diethyl ether (3×25 ml)
  3. washThe combined organic phases were washed with water (25 ml) and aq. sat. NaCl solution (25 ml)
  4. dry with materialdried over magnesium sulphate
  5. customAfter removing the solvent in a vacuum
  6. custompurifying the residue by column chromatography (SiO2, diethyl ether/hexane=3:1)

出典と根拠

ORDレコード
ord-889a619831874dbe833548ec6ad8df20
出典データセット
uspto-grants-2012_12
特許番号
US08334315B2

関連ノート

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