Acetic Anhydride → (E)-methyl 1-acetyl-3-(ethoxy(phenyl)methylene)-2-oxo-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine-6-carboxylate

HRID 577800ノート

反応式

HRID 577800 の反応式
[O:1]=[C:2]1[NH:10][C:9]2[CH:8]=[C:7]([C:11]([O:13][CH3:14])=[O:12])[N:6]=[CH:5][C:4]=2[CH2:3]1.[CH3:15][C:16](OC(C)=O)=[O:17].[CH3:22][CH2:23][O:24][C:25](OCC)(OCC)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1(C)C=CC=CC=1>[C:16]([N:10]1[C:9]2[CH:8]=[C:7]([C:11]([O:13][CH3:14])=[O:12])[N:6]=[CH:5][C:4]=2/[C:3](=[C:25](\[O:24][CH2:23][CH3:22])/[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)/[C:2]1=[O:1])(=[O:17])[CH3:15]

参加物

5

反応物 3

HCID 7918Acetic AnhydrideHCID 74268Benzene, (triethoxymethyl)-HCID 72207279Methyl 5-aza-2-oxindole-6-carboxylate

生成物 1

HCID 89719567(E)-methyl 1-acetyl-3-(ethoxy(phenyl)methylene)-2-oxo-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine-6-carboxylate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
85 °C

実験手順

Step-1: To a solution of methyl 2-oxo-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (10 mg, 0.052 mmol) in toluene (5 mL) was added Ac2O (15 mg, 0.156 mmol) and triethyl orthobenzoate (35 mg, 0.156 mmol) at room temperature. The reaction mixture was heated stirred at 85° C. for 3 h. The solvent was evaporated under reduced pressure and the resulting residue was purified by silica gel column chromatography using 5% acetone in dichloromethane to afford (E)-methyl 1-acetyl-3-(ethoxy(phenyl)methylene)-2-oxo-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine-6-carboxylate as yellow solid. 1H NMR (CDCl3, 400 MHz) δ 9.15 (s, 1H), 8.67 (s, 1H), 7.52-7.59 (m, 5H), 4.06 (dd, J=13.9, 7 Hz), 3.89 (s, 3H), 2.45 (s, 3H), 1.37 (t, J=7 Hz, 3H).

後処理

  1. temperatureThe reaction mixture was heated
  2. customThe solvent was evaporated under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-c9bf65d5d50f4b4f8e2c9bd65e7a6489
出典データセット
uspto-grants-2015_05
特許番号
US09040555B2

反応ノート

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