Lithium borohydride → N-[6-chloro-4-(hydroxymethyl)pyridin-2-yl]-N-propylmethanesulfonamide

HRID 552889Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 552889
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N:12]([S:16]([CH3:19])(=[O:18])=[O:17])[CH2:13][CH2:14][CH3:15])[N:11]=1)[C:5](OC)=[O:6].[Li+].[BH4-]>C1COCC1>[Cl:1][C:2]1[N:11]=[C:10]([N:12]([CH2:13][CH2:14][CH3:15])[S:16]([CH3:19])(=[O:17])=[O:18])[CH:9]=[C:4]([CH2:5][OH:6])[CH:3]=1

Komponenten

4

Edukt 2

HCID 4148881Lithium borohydrideHCID 57434730Methyl 2-chloro-6-[(methylsulfonyl)(propyl)amino]isonicotinate

Produkt 1

HCID 57775667N-[6-chloro-4-(hydroxymethyl)pyridin-2-yl]-N-propylmethanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-chloro-6-[(methylsulfonyl)(propyl)amino]isonicotinate (3.5 g, 11.5 mmol) in THF (50 mL) cooled to 0° C. was added LiBH4 (17.2 mL, 34.4 mmol, 2 M in THF). After 10 min, the reaction mixture was allowed to warm to rt and stirred for 3.5 h. The reaction mixture was carefully quenched with EtOAc, MeOH and water. Following dilution with EtOAc, the organic layer was extracted, washed with brine, dried over sodium sulfate and concentrated in vacuo to provide N-[6-chloro-4-(hydroxymethyl)pyridin-2-yl]-N-propylmethanesulfonamide which was used as is in the bromination step.

Aufarbeitung

  1. customThe reaction mixture was carefully quenched with EtOAc, MeOH and water
  2. extractionthe organic layer was extracted
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-97725a5e32ea42428a7f70cd80a9f677
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951949B2

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