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

HRID 577800Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 85 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-c9bf65d5d50f4b4f8e2c9bd65e7a6489
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040555B2

Reaction notes

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