Lithium triethylborohydride → 2-(3-chloro-2-(hydroxymethyl)phenyl)-6-cyclopropyl-8-fluoroisoquinolin-1(2H)-one

HRID 2069862Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2069862
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([F:23])[CH:14]=[C:15]([CH:20]4[CH2:22][CH2:21]4)[CH:16]=3)[C:11]2=[O:24])[C:3]=1[CH:4]=[O:5].[Li+].[B-](CC)(CC)CC>C1COCC1>[Cl:1][C:2]1[C:3]([CH2:4][OH:5])=[C:6]([N:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([F:23])[CH:14]=[C:15]([CH:20]4[CH2:22][CH2:21]4)[CH:16]=3)[C:11]2=[O:24])[CH:7]=[CH:8][CH:9]=1

Komponenten

4

Edukt 2

HCID 23712863Lithium triethylborohydrideHCID 594737722-chloro-6-(6-cyclopropyl-8-fluoro-1-oxoisoquinolin-2(1H)-yl)benzaldehyde

Produkt 1

HCID 594737982-(3-chloro-2-(hydroxymethyl)phenyl)-6-cyclopropyl-8-fluoroisoquinolin-1(2H)-oneAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of compound III (0.26 g, 0.76 mmol) in 15 ml dry THF which was cooled at 0° C. in an ice bath, was added a solution of superhydride 1M (1.5 ml, 1.5 mmol) in THF. After stirring for 0.5 hour at 0° C. the reaction was quenched with saturated ammonium chloride and diluted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate and concentrated to give 0.25 g (96% yield) of IV which was used in the next step without further purification.

Aufarbeitung

  1. customwas quenched with saturated ammonium chloride
  2. additiondiluted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-746ca1ecb9db4d68a6f9dcb83a0cff55
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299077B2

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