Dichloromethane → ethyl 2-(7-acetamido-4-fluoro-1H-indol-3-yl)-2-oxoacetate

HRID 2097670ノート

反応式

HRID 2097670 の反応式
[F:1][C:2]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[C:7]2[C:3]=1C=C[NH:6]2.[Al+3].[Cl-].[Cl-].[Cl-].Cl[C:20]([C:22]([CH2:24][CH3:25])=[O:23])=[O:21].[C:26]([O-:29])(O)=O.[Na+].[CH2:31](Cl)Cl>>[C:12]([NH:11][C:8]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]2[C:7]=1[NH:6][CH:25]=[C:24]2[C:22](=[O:23])[C:20]([O:29][CH2:26][CH3:31])=[O:21])(=[O:14])[CH3:13]

参加物

6

反応物 5

HCID 6344Dichloromethane2 回HCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) Chloride2 回HCID 11007880Butanoyl chloride, 2-oxo-HCID 66728479N-(4-Fluoro-1H-indol-7-yl)acetamide

生成物 1

HCID 66728362ethyl 2-(7-acetamido-4-fluoro-1H-indol-3-yl)-2-oxoacetate

実験手順

N-(4-fluoro-1H-indol-7-yl)acetamide (1 eq.) was added to a suspension of AlCl3 (1 eq.) in CH2Cl2 (100 ml). After 15 min, a premixed suspension of AlCl3 (2 eq.) and ClCOCOEt (2 eq.) in CH2Cl2 was added and stirring was continued at room temperature for 1 hour before iced saturated NaHCO3 solution was added. The aqueous phase was extracted with EtOAc. The combined organic layer was dried over MgSO4. After filtration and concentration, the crude product was purified by silica gel column chromatography to afford ethyl 2-(7-acetamido-4-fluoro-1H-indol-3-yl)-2-oxoacetate. MS m/z: (M+H)+ calc'd for C14H14FN2O4:293.09. Found 293.11. HPLC retention time: 0.98 minutes (column E, solvent system II). 1H NMR (300 MHz, CD3OD) 8.32 (s, 1H), 7.16 (m, 1H), 6.94 (m, 1H), 4.43 (q, 2H, J=7.2 Hz), 2.24 (s, 3H), 1.39 (t, 3H, J=7.2 Hz).

後処理

  1. additionwas added
  2. additionwas added
  3. extractionThe aqueous phase was extracted with EtOAc
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. filtrationAfter filtration and concentration
  6. customthe crude product was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-bf2e4f71ba1f4212a447961092e16718
出典データセット
uspto-grants-2013_05
特許番号
US08450361B2

反応ノート

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