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

HRID 2415089Notes

Reaction equation

HRID 2415089 reaction equation
[C:1]([C:6]1[CH:7]=[C:8]2[C:12](=[N:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9]2)([O:3][CH2:4][CH3:5])=[O:2].[CH2:16]([O:18][CH:19](OC(=O)C)OCC)[CH3:17].C(OCC)C>C(O)(=O)C>[C:1]([C:6]1[CH:7]=[C:8]2[C:12](=[N:13][CH:14]=1)[NH:11][C:10](=[O:15])[C:9]2=[CH:19][O:18][CH2:16][CH3:17])([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 84166Methanol, 1,1-diethoxy-, 1-acetateHCID 15504072ethyl 2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

Product 1

HCID 538705645-Carboethoxy-3-ethoxymethylene-7-azaoxindoleYield 69%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

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 h. 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).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customto precipitate a beige solid
  3. filtrationthat was collected by filtration (35 mg, 69% yield)

Sources & evidence

ORD record
ord-073f5407b5a747ae9a21ec60439cb693
Source dataset
uspto-grants-2004_11
Patent number
US06818632B2

Reaction notes

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