Reaktion #166664

Reaktionsgleichung

sulfurous dichloride

(5-(benzyloxy)-6-methylpyridin-2-yl)methanol

3-bromo-4-nitro-1H-indazole

K2CO3

→

desired product

Ausbeute 87.0%

1-((5-(benzyloxy)-6-methylpyridin-2-yl)methyl)-3-bromo-4-nitro-1H-indazole

Ausbeute 87.0%

Lösungsmittel

DCM

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigesolvent was removed under reduced pressure
2. 2
   workup.STIRRINGThe reaction mixture was stirred for 18 hours
3. 3
   SonstigeThe solvent was removed under reduced pressure
4. 4
   workup.ADDITIONThe residue was diluted with water (50 mL)
5. 5
   Extraktionextracted with EtOAc
6. 6
   TrocknenThe combined organic extracts were dried (Na2SO4)
7. 7
   Einengenconcentrated
8. 8
   Sonstigethe residue was purified by silica gel flash chromatography (1:3 EtOAc/hexanes)

Vorschrift

To (5-(benzyloxy)-6-methylpyridin-2-yl)methanol (3.51 g, 15.3 mmol, Prepared as described in U.S. Pat. No. 3,952,101) in DCM (10 mL) was added sulfurous dichloride (10.9 g, 91.9 mmol). The reaction mixture was stirred for 3 hours, and then solvent was removed under reduced pressure. To the resulting solid was added 3-bromo-4-nitro-1H-indazole (3.71 g, 15.3 mmol), K2CO3 (6.35 g, 45.9 mmol) and anhydrous DMF (20 mL). The reaction mixture was stirred for 18 hours. The solvent was removed under reduced pressure. The residue was diluted with water (50 mL) and extracted with EtOAc. The combined organic extracts were dried (Na2SO4), and concentrated, and the residue was purified by silica gel flash chromatography (1:3 EtOAc/hexanes) to give desired product (87%).

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