Sodium Methoxide → 6-[5-Fluoro-4-methoxy-2-(2,2,2-trifluoro-ethyl)-phenyl]-1-(tetrahydro-pyran-2-yl)-1H-indazole-3-carboximidic acid methyl ester

HRID 2038737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2038737
[F:1][C:2]1[C:3]([O:30][CH3:31])=[CH:4][C:5]([CH2:25][C:26]([F:29])([F:28])[F:27])=[C:6]([C:8]2[CH:16]=[C:15]3[C:11]([C:12]([C:23]#[N:24])=[N:13][N:14]3[CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)=[CH:10][CH:9]=2)[CH:7]=1.[CH3:32][O-:33].[Na+]>CO>[CH3:32][O:33][C:23]([C:12]1[C:11]2[C:15](=[CH:16][C:8]([C:6]3[CH:7]=[C:2]([F:1])[C:3]([O:30][CH3:31])=[CH:4][C:5]=3[CH2:25][C:26]([F:29])([F:28])[F:27])=[CH:9][CH:10]=2)[N:14]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[N:13]=1)=[NH:24]

Komponenten

4

Edukt 2

HCID 10942334Sodium MethoxideHCID 712380616-[5-Fluoro-4-methoxy-2-(2,2,2-trifluoro-ethyl)-phenyl]-1-(tetrahydro-pyran-2-yl)-1H-indazole-3-carbonitrile

Produkt 1

HCID 866762786-[5-Fluoro-4-methoxy-2-(2,2,2-trifluoro-ethyl)-phenyl]-1-(tetrahydro-pyran-2-yl)-1H-indazole-3-carboximidic acid methyl esterAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 6-[5-fluoro-4-methoxy-2-(2,2,2-trifluoro-ethyl)-phenyl]-1-(tetrahydro-pyran-2-yl)-1H-indazole-3-carbonitrile (Preparation 37, 1.737 g, 4.00 mmol) in methanol (40 mL) was added sodium methoxide (648 mg, 12.0 mmol) and the reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was partitioned between EtOAc (50 mL) and water (50 mL) and the aqueous layer was extracted with further EtOAc (2×50 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to give the title compound as an oily solid (1.64 g) in an 88% yield.

Aufarbeitung

  1. customThe reaction mixture was partitioned between EtOAc (50 mL) and water (50 mL)
  2. extractionthe aqueous layer was extracted with further EtOAc (2×50 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-31a1e755603441a198955006013012b4
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575336B2

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