Hydrochloric Acid → N-(4-Acetyl-2-fluorophenyl)methanesulfonamide

HRID 238932

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HRID 238932 반응식
[F:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11].[C:14]([O-])(=[O:16])[CH3:15].[Tl+].C(OC=C)CCC.Cl>CN(C=O)C.C1COCC1.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[CH:7]=[C:6]([C:14](=[O:16])[CH3:15])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11]

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 8108Butyl vinyl etherHCID 11247thallium(I) acetateHCID 19785608N-(2-Fluoro-4-iodophenyl)methanesulfonamide

생성물 1

HCID 58755745N-(4-Acetyl-2-fluorophenyl)methanesulfonamide

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
95 °C

실험 절차

A mixture of N-(2-Fluoro-4-iodophenyl)methanesulfonamide (13-3, 5 mmol) and palladium(II)acetate (0.15 nM, 0.034 g), 1,3-bisdiphenyl phosphinoprophan (0.3 mM, 0.124 g), thallium(I)acetate (5.5 mM, 1.450 g) and butylvinyl ether (10 mM, 1.3 mL) in DMF (10 mL) was heated at 95° C. for 19 h. The reaction mixture was cooled to room temperature, diluted with THF, treated with 10% HCl (10 mL) and stirred at room temperature. A mixture was diluted with EtOAc, washed with ammonium chloride solution three times and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes as eluant to 3′-Fluoro-4′-(methylsulfonylamino)acetophenone (13-6, LJO-363).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with ammonium chloride solution three times
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel

출처 및 근거

ORD 기록
ord-1e154d2223aa4f1f859ba08d87aad887
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642657B2

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