Acetic Acid → ethyl 5-(2-methoxyethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

HRID 553567ノート

反応式

HRID 553567 の反応式
[K].[CH3:2][O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH2:13][C:14](=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([N+:21]([O-])=O)=[CH:9][N:8]=1.C(O)(=O)C.[H][H].C(O)C(F)(F)F>CO.[OH-].[Pd+2].[OH-]>[CH3:2][O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]2[CH:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[NH:21][C:10]2=[CH:9][N:8]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 64092,2,2-TrifluoroethanolHCID 67461922Ethyl 3-[2-(2-methoxyethoxy)-5-nitropyridin-4-yl]-2-oxopropionate potassium saltHCID 178418361HCID 178418361、化合物

生成物 1

HCID 59820057ethyl 5-(2-methoxyethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 887Methanol溶媒

実験手順

3.5 g of dried ethyl 3-[2-(2-methoxyethoxy)-5-nitropyridin-4-yl]-2-oxopropionate potassium salt are dissolved in 50 ml of MeOH, and 2 ml of acetic acid are added. After the addition of 500 mg of palladium hydroxide/C 20%, the mixture is stirred under 1 atm of hydrogen. After 5 h, a further 200 mg of catalyst and 0.75 ml of trifluoroethanol are added. After a further 3 h, all volatile components are removed under reduced pressure and 20 ml of sat. sodium bicarbonate solution are added and the mixture is extracted with ethyl acetate. The organic phase is dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is purified by flash chromatography on silica gel (n-heptane/ethyl acetate=1:2). This gives ethyl 5-(2-methoxyethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate as a yellowish solid. C13H16N2O4 (264.28), MS (ESI): 265 (M+H+).

後処理

  1. waitAfter a further 3 h
  2. customall volatile components are removed under reduced pressure and 20 ml of sat. sodium bicarbonate solution
  3. additionare added
  4. extractionthe mixture is extracted with ethyl acetate
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. customthe solvent is removed under reduced pressure
  7. customThe residue is purified by flash chromatography on silica gel (n-heptane/ethyl acetate=1:2)

出典と根拠

ORDレコード
ord-96fd6bfae9a442b1afffa004dd3bf546
出典データセット
uspto-grants-2011_11
特許番号
US08048901B2

反応ノート

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