Reaktion #1272206

Reaktionsgleichung

2-(6-tert-Butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-6-chloro-benzaldehyde

2-(6-tert-Butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-chlorobenzaldehyde

NaBH4

→

101j

Ausbeute 76.2%

6-tert-Butyl-2-(3-chloro-2-(hydroxymethyl)phenyl)-8-fluorophthalazin-1(2H)-one

Ausbeute 76.2%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITION1 mL of iPA was added to the solution
2. 2
   TemperaturThe resulting solution was cooled to 4° C.
3. 3
   workup.STIRRINGAfter 30 min stirring
4. 4
   Sonstigethe reaction was quenched
5. 5
   workup.ADDITIONby adding H2O (2 mL)
6. 6
   ExtraktionThe aqueous layer was extracted with CH2Cl2 (2×5 mL)
7. 7
   Waschenwashed with brine
8. 8
   Trocknendried over MgSO4
9. 9
   EinengenThe filtrate was concentrated
10. 10
    Sonstigeto give a residue which
11. 11
    Sonstigewas purified by silica gel chromatography
12. 12
    Wascheneluting with 0-20% EtOAc/CH2Cl2

Vorschrift

2-(6-tert-Butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-6-chloro-benzaldehyde 101i (519 mg, 1.4 mmol) was dissolved in DCM (2 mL) with stirring at room temperature, and then 1 mL of iPA was added to the solution. The resulting solution was cooled to 4° C., and NaBH4 (27 mg, 0.7 mmol) was added in one portion. After 30 min stirring, the reaction was quenched by adding H2O (2 mL). The aqueous layer was extracted with CH2Cl2 (2×5 mL), washed with brine and dried over MgSO4. The filtrate was concentrated to give a residue which was purified by silica gel chromatography eluting with 0-20% EtOAc/CH2Cl2 to furnish 101j as a white solid (385 mg, 72%). MS: [M+H]+: 361

Quelle