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

HRID 577800노트

반응식

HRID 577800 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
85 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c9bf65d5d50f4b4f8e2c9bd65e7a6489
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040555B2

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