Methyl iodide → 6-(2,4-Difluorophenoxy)-4-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1,4-dihydro-pyrazolo[4,3-b]pyridin-5-one

HRID 2114556Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2114556
[F:1][C:2]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:3]=1[O:4][C:5]1[C:10](=[O:11])[NH:9][C:8]2[CH:12]=[N:13][N:14]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:7]=2[CH:6]=1.[H-].[Na+].[CH3:30]I>CN(C)C=O.C(OCC)(=O)C.O>[F:1][C:2]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:3]=1[O:4][C:5]1[C:10](=[O:11])[N:9]([CH3:30])[C:8]2[CH:12]=[N:13][N:14]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:20])[CH3:21])[C:7]=2[CH:6]=1

Komponenten

7

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 598129756-(2,4-Difluorophenoxy)-1-(2-trimethylsilanyl-ethoxymethyl)-1,4-dihydro-pyrazolo[4,3-b]pyridin-5-one

Produkt 1

HCID 598128336-(2,4-Difluorophenoxy)-4-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1,4-dihydro-pyrazolo[4,3-b]pyridin-5-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a 0° C. solution of 6-(2,4-difluorophenoxy)-1-(2-trimethylsilanyl-ethoxymethyl)-1,4-dihydro-pyrazolo[4,3-b]pyridin-5-one (98 mg, 0.249 mmol) in dimethylformamide (1 mL) was added sodium hydride (60% dispersion in oil, Aldrich) (15 mg, 1.5 eq) and the resulting mixture was stirred at for 30 minutes, after which methyl iodide (25 μL, 1.5 eq) was added and the mixture was stirred additional 1 hour with warming from 0° C. to room temperature. The reaction mixture was diluted with ethyl acetate (35 mL) and water (25 mL). The organic layer was separated, washed with water (2×25 mL) and brine (1×25 mL), dried over magnesium sulfate, filtered and concentrated to give the title compound as a tan powder (118 mg, (M+H)+=408).

Aufarbeitung

  1. stirringthe mixture was stirred additional 1 hour
  2. temperaturewith warming from 0° C. to room temperature
  3. customThe organic layer was separated
  4. washwashed with water (2×25 mL) and brine (1×25 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0271b47186694d379a1bbedac57a0bc4
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07435731B2

Notizen zur Reaktion

Wird geladen…