Nitrogen → HCID 66928958, compound

Participants

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of methanesulfonic acid 5-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-3-ylmethyl ester (271 mg, 0.99 mmol) in acetone (6.0 mL) was added, under inert atmosphere (N2) to a solution of 4-nitro-1H-pyrazole (126 mg, 0.99 mmol) in acetone (6.0 mL). K2CO3 (691 mg, 4.95 mmol) followed by TBA iodide (64 mg, 0.20 mmol) were added to the reaction mixture, which 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 (10:1 to 2:1 hept-EA) gave the title compound as a pale yellow oil. TLC: rf (50:50 hept-EA)=0.1. LC-MS-conditions 02: tR=0.74 min; [M+H]+=291.11.

Provenance & Evidence