Sodium borohydride → 1-[5-Chloro-8-(2-fluorophenyl)quinolin-7-yl]ethanol

HRID 1192490Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1192490
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=[O:14])[CH3:13])[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:11]=[C:10]([CH:12]([OH:14])[CH3:13])[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 672495351-[5-Chloro-8-(2-fluorophenyl)quinolin-7-yl]ethanone

Produkt 1

HCID 672484331-[5-Chloro-8-(2-fluorophenyl)quinolin-7-yl]ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a mixture of 1-[5-chloro-8-(2-fluorophenyl)quinolin-7-yl]ethanone (0.032 g, 0.11 mmol) in methanol (0.3 mL) was added sodium tetrahydroborate (0.0040 g, 0.11 mmol). The reaction was stirred at room temperature for 1 hour, quenched with saturated sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and then concentrated to dryness under reduced pressure. The resulting residue was used in next step (33 mg, 100%). LCMS calculated for C17H14ClFNO(M+H)+: m/z=302.1; found: 302.0.

Aufarbeitung

  1. customquenched with saturated sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c7520f0704c043368ae4b9e7e47c048e
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680108B2

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