تفاعل #166664

معادلة التفاعل

sulfurous dichloride

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

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

K2CO3

→

desired product

المردود 87.0%

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

المردود 87.0%

المذيبات

DCM

DMF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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%).

المصدر