Diethyl Ether → Ethyl 3-[(Z)-ethoxymethylidene]-2-oxo-1,2-dihydro-3H-pyrrolo[2,3-b]pyridine-5-carboxylate

HRID 1168237Notes

Reaction equation

[O:1]=[C:2]1[NH:15][C:5]2=[N:6][CH:7]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:9]=[C:4]2[CH2:3]1.[C:16]([O:19][CH:20](OCC)OCC)(=O)[CH3:17].C(OCC)C>C(O)(=O)C>[CH2:16]([O:19]/[CH:20]=[C:3]1\[C:2](=[O:1])[NH:15][C:5]2[C:4]\1=[CH:9][C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:7][N:6]=2)[CH3:17]

Participants

Conditions

Temperature: 110 °C

Procedure

Ethyl 2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (0.040 g, 0.19 mmol) and diethoxymethyl acetate (0.16 mL, 0.97 mmol) were combined and dissolved in acetic acid (1 mL). The reaction was warmed to 110° C. and stirred at this temperature for 1 h. The reaction was cooled to room temperature, and diethyl ether was added to precipitate the title compound as a beige solid that was collected by filtration (35 mg, 69% yield). 1H NMR 400 MHz (DMSO-d6): δ 11.30 (s, 1H); 8.58 (s, 1H); 8.05 (s, 1H); 7.93 (s, 1H); 4.44 (m, 2H); 4.28 (m, 2H); 1.35 (m, 3H); 1.28 (m, 3H).

Workup

temperatureThe reaction was cooled to room temperature
customto precipitate the title compound as a beige solid
filtrationthat was collected by filtration (35 mg, 69% yield)

Sources & evidence

ORD record: ord-d71f024600a349ecae3d22941c7d9436
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06624171B1

Reaction notes

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