Reaktion #2152151

Reaktionsgleichung

N2

K2CO3

iodide

methanesulfonic acid 6-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-2-ylmethyl ester

N2

5-nitro-1H-pyrazole

→

title compound

2-(2-Methyl-[1,3]dioxolan-2-yl)-6-(3-nitro-pyrazol-1-ylmethyl)-pyridine

Lösungsmittel

acetone

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed under reduced pressure
2. 2
   workup.ADDITIONWater (10 mL) and EA (10 mL) were added
3. 3
   ExtraktionThe aq. layer was extracted with EA (10 mL)
4. 4
   Trocknenextracts were dried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Sonstigethe solvents were removed under reduced pressure
7. 7
   SonstigePurification of the residue by FC (30:10 to 50:50 hept-EA)

Vorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of methanesulfonic acid 6-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-2-ylmethyl ester (273 mg, 1.00 mmol) in acetone (4.0 mL) was added, under inert atmosphere (N2) to a solution of 5-nitro-1H-pyrazole (115 mg, 1.00 mmol) in acetone (4.0 mL). K2CO3 (698 mg, 5.00 mmol) and TBA iodide (64 mg, 0.20 mmol) were added and the reaction mixture was stirred at rt for 5 h. The solvent was removed under reduced pressure. Water (10 mL) and EA (10 mL) were added. The aq. layer was extracted with EA (10 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (30:10 to 50:50 hept-EA) gave the title compound as a light brown solid. TLC: rf (50:50 hept-EA)=0.16. LC-MS-conditions 02: tR=0.87 min; [M+H]+=291.35.

Quelle