Methanol → Gsk-2881078

HRID 1851119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1851119
CS[CH2:3][C@H:4]([N:6]1[C:14]2[C:9](=[C:10]([C:17]([F:20])([F:19])[F:18])[C:11]([C:15]#[N:16])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH3:5].O[O:22][S:23]([O-:25])=O.[K+].[CH3:27]O>O>[CH3:27][S:23]([CH2:5][C@H:4]([N:6]1[C:14]2[C:9](=[C:10]([C:17]([F:19])([F:18])[F:20])[C:11]([C:15]#[N:16])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH3:3])(=[O:25])=[O:22]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 86709175HCID 86709175, Verbindung

Produkt 1

HCID 86709174Gsk-2881078

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To an ice-cold solution of (R)-1-(1-(methylthio)propan-2-yl)-4-(trifluoromethyl)-1H-indole-5-carbonitrile (0.560 g, 1.88 mmol) in MeOH (10 mL) was added a solution of Oxone (4.04 g, 6.57 mmol) in water (10 mL). After 50 min, the reaction mixture was diluted with water (30 mL) and extracted with EtOAc (50 mL). The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The residue was chromatographed over silica gel using 100% CH2Cl2 to give (R)-1-(1-(methylsulfonyl)propan-2-yl)-4-(trifluoromethyl)-1H-indole-5-carbonitrile as a white foam that was crystallized from CH2Cl2/hexanes to afford a white solid (0.508 g, 79% yield): 1H NMR (400 MHz, DMSO-d6) δ 8.17 (d, J=8.6 Hz, 1H), 8.12 (d, J=3.5 Hz, 1H), 7.81 (d, J=8.5 Hz, 1H), 6.87-6.84 (m, 1H), 5.43-5.35 (m, 1H), 4.01 (dd, J=14.8, 8.6 Hz, 1H), 3.83 (dd, J=14.8, 4.9 Hz, 1H), 2.77 (s, 3H), 1.59 (d, J=6.8 Hz, 3H); MS (ESI): m/z 331 (M+H).

Aufarbeitung

  1. extractionextracted with EtOAc (50 mL)
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed over silica gel using 100% CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-ad2bc5fb650e41159de949603ccdbdad
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957104B2

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