Ethyl Acetate → 4-Methoxy-7-pyrazinyl-6-azaindol-3-yl-oxoacetic acid methyl ester

HRID 1394426Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1394426
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:15]=[N:14][C:13]([C:16]2[CH:21]=[N:20][CH:19]=[CH:18][N:17]=2)=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2.C([O-])(=[O:24])C.[NH4+].C[CH2:28][O:29][C:30]([CH3:32])=[O:31]>C(Cl)Cl.C[N+]([O-])=O>[CH3:28][O:29][C:30](=[O:31])[C:32]([C:9]1[C:8]2[C:12](=[C:13]([C:16]3[CH:21]=[N:20][CH:19]=[CH:18][N:17]=3)[N:14]=[CH:15][C:7]=2[O:6][CH3:5])[NH:11][CH:10]=1)=[O:24]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 517165Ammonium AcetateHCID 6451240Aluminum(III) ChlorideHCID 207912514-Methoxy-7-(pyrazin-2-YL)-1H-pyrrolo[2,3-C]pyridine

Produkt 1

HCID 670462744-Methoxy-7-pyrazinyl-6-azaindol-3-yl-oxoacetic acid methyl esterAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23431834Dichloromethane nitromethaneLösungsmittel

Versuchsvorschrift

To a mixture of AlCl3 (3.09 g, 23.2 mmol) in 20 mL of CH2Cl2-MeNO2 (4: 1) was added 4-methoxy-7-pyrazinyl-6-azaindole (0.525 g, 2.32 mmol) as a solid. To the resulting burgundy solution was added methyl oxalyl chloride (0.853 mL, 9.28 mmol) dropwise and then the mixture was stirred at room temperature for 1.5 h. The reaction mixture was then carefully poured into cold 20% aqueous ammonium acetate and EtOAc was added. The resulting emulsion was filtered and the residue was washed with additional EtOAc. The organic phase was separated and the aqueous phase was again extracted with EtOAc. The combined organic phase was dried (MgSO4) and evaporated to give 4-methoxy-7-pyrazinyl-6-azaindol-3-yl-oxoacetic acid methyl ester (0.494 g, 68%) as a brownish solid: LCMS m/e 313 (M+H)+. This material (0.456 g, 1.46 mmol) was taken up in 20 mL of MeOH, 1M K2CO3 (5.84 mL, 5.84 mmol) was added and the mixture was stirred at room temperature for 30 min. The solution was then diluted with water (4 mL) and concentrated in vacuo. The resulting aqueous solution was cooled at 0° C. and acidified to pH 1-2 with 6N HCl. This gave a bright yellow precipitate which was filtered, washed with cold 0.1N HCl and ether and dried in vacuo to give the title compound (0.309 g, 71%) as a yellow solid:

Aufarbeitung

  1. additionwas added
  2. filtrationThe resulting emulsion was filtered
  3. washthe residue was washed with additional EtOAc
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was again extracted with EtOAc
  6. dry with materialThe combined organic phase was dried (MgSO4)
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-afa9f0e7f2ae43afb8c72b7d1acc40a6
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07348337B2

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