Bis(trifluoroacetoxy)iodobenzene → 3-(2,4-Difluoro-phenylsulfanyl)-6-methanesulfonyl-1H-indole-2-carboxylic acid methyl ester

HRID 985555

반응식

HRID 985555 반응식
[C:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:8]=2)([O:3][CH3:4])=[O:2].[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[SH:26].C1C=CC(I(OC(C(F)(F)F)=O)OC(C(F)(F)F)=O)=CC=1>FC(F)(F)C(O)C(F)(F)F>[CH3:4][O:3][C:1]([C:5]1[NH:6][C:7]2[C:12]([C:13]=1[S:26][C:20]1[CH:21]=[CH:22][C:23]([F:25])=[CH:24][C:19]=1[F:18])=[CH:11][CH:10]=[C:9]([S:14]([CH3:17])(=[O:15])=[O:16])[CH:8]=2)=[O:2]

참가 물질

5

반응물 3

HCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 27370732,4-Difluorobenzene-1-thiolHCID 7141904methyl 6-(methylsulfonyl)-1H-indole-2-carboxylate

생성물 1

HCID 114180743-(2,4-Difluoro-phenylsulfanyl)-6-methanesulfonyl-1H-indole-2-carboxylic acid methyl ester수율 88%

시약·촉매·용매 1

HCID 135291,1,1,3,3,3-Hexafluoro-2-propanol용매

실험 절차

A solution of 2-carbomethoxy-6-methylsulfonylindole (750 mg, 2.8 mmol), in 10 mL hexafluoroisopropanol was treated with 2,4-difluorothiophenol (7.5 mmol) followed by addition of PIFA (5.6 mmol). The dark colored solution was stirred overnight then partitioned between methylene chloride and water. After concentration of the methylene chloride layer to 20 mL the product was precipitated by addition of 30 mL hexane. An 88% yield of 3-(2,4-difluoro-phenylsulfanyl)-6-methanesulfonyl-1H-indole-2-carboxylic acid methyl ester was obtained.

후처리

  1. customthen partitioned between methylene chloride and water
  2. customAfter concentration of the methylene chloride layer to 20 mL the product was precipitated by addition of 30 mL hexane

출처 및 근거

ORD 기록
ord-93ee1af161384b4ab582c44460df93e0
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06872744B2

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