Tetrahydrofuran → N-(3,6-dichloropyridazin-4-yl)-4-fluorobenzenesulfonamide

Temperature

0 °C

To a 50 mL round-bottomed flask was added 3,6-dichloropyridazin-4-amine (148 mg, 902 μmol), sodium bis(trimethylsilyl)amide (365 μl, 1805 μmol) and THF (3 mL) at 0° C. The mixture was stirred at 0° C. for 30 min. 4-fluorobenzene-1-sulfonyl chloride (263 mg, 1354 μmol) was then added. The mixture was stirred at 0° C. for 1 hour. The reaction mixture was diluted with satd NH4Cl (10 mL) and extracted with EtOAc (3×30 mL). The combined organic extracts were washed with satd NaCl (5 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography (5% MeOH/EtOAc) to give N-(3,6-dichloropyridazin-4-yl)-4-fluorobenzenesulfonamide (252 mg, 86.7% yield). MS (ESI positive ion) m/z: 323 (M+1). 1H NMR (300 MHz, DMSO-d6) δ ppm 6.95 (s, 1H) 7.23-7.35 (m, 2H) 7.74-7.84 (m, 2H)

1. stirringThe mixture was stirred at 0° C. for 1 hour
2. extractionextracted with EtOAc (3×30 mL)
3. washThe combined organic extracts were washed with satd NaCl (5 mL)
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customthe residue was purified by silica gel chromatography (5% MeOH/EtOAc)

ORD record

ord-25c09a5877634eaeb537f226b680db5a

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07820665B2