反应详情

温度

20 °C

To a solution of crude 4-(bromomethyl)-N-(2,4-dimethylphenyl)-N-isobutylbenzenesulfonamide (100 mg, 0.122 mmol) and pyridine-4-ylmethanol (13.30 mg, 0.122 mmol) in 2-Methyltetrahydrofuran (2-MeTHF) (1 mL) and dimethyl sulfoxide (DMSO) (0.5 mL) stirred in air at RT was added solid sodium hydride (4.87 mg, 0.122 mmol) in one charge, tip of spatula. The reaction mixture was stirred at 20° C. for 16 hours. Reaction was carefully quenched with methanol (0.5 mL) and water (0.5 mL) and evaporated in vacuo to give a residue in DMSO. This was diluted with dichloromethane (10 mL) and water (10 mL) and stirred vigorously for 10 min. The layers were separated by hydrophobic frit and the organic fraction evaporated to give the crude product. The samples were dissolved in 1:1 MeOH:DMSO 1 mL and purified by mass directed autoprep on Sunfire C18 column using acetonitrile:water with a formic acid modifier. The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus to give the required product N-(2,4-dimethylphenyl)-N-isobutyl-4-((pyridine-4-ylmethoxy)methyl)benzenesulfonamide (4.8 mg, 10.94 μmol, 8.98% yield)

1. additioncharge
2. customReaction
3. customwas carefully quenched with methanol (0.5 mL) and water (0.5 mL)
4. customevaporated in vacuo
5. customto give a residue in DMSO
6. stirringstirred vigorously for 10 min
7. customThe layers were separated by hydrophobic frit
8. customthe organic fraction evaporated
9. customto give the crude product
10. customDMSO 1 mL and purified by mass
11. customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus