Diethyl Ether → 5-Carboethoxy-3-ethoxymethylene-7-azaoxindole

Participants

Role	Name	HCID	Charge
Reactant	Diethyl Ether	HCID 3283	—
Reactant	Methanol, 1,1-diethoxy-, 1-acetate	HCID 84166	—
Reactant	ethyl 2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate	HCID 15504072	—
Solvent	Acetic Acid	HCID 176	—
Product	5-Carboethoxy-3-ethoxymethylene-7-azaoxindole	HCID 53870564	69%

Reaction Conditions

Temperature	110 °C

Reaction Steps

5-Carboethoxy-7-azaoxindole (0.040 g, 0.19 mmol) and diethoxymethylacetate (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 hour. The reaction was cooled to room temperature and diethyl ether was added to precipitate a beige solid that was collected by filtration (35 mg, 69% yield). 1H NMR 400 MHz (DMSO-d6) δ11.30 (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).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06369086B1
Source dataset	uspto-grants-2002_04
ORD ID	ord-e7a7f3b7ffd440bdb5f5b1f2c7900452
Source note	uspto-grants-2002_04