4-Toluenesulfonyl chloride → 6-Methylpyridazine-3-carbonitrile

To a stirring solution of 3-methylpyridazine (1.1 g, 11.80 mmol) in dichloromethane (20 mL) was added AlCl3 (0.05 g) followed by trimethylsilylcyanide (2.1 g, 21.1 mmol). After 20 min, a solution of p-toluenesulfonyl chloride (3.8 g, 20.1 mmol) in dichloromethane (5 mL) was added slowly and the solution was stirred for 16 h. The solvent was removed in vacuo and ethanol (10 ml) was added and stirred for 15 min, then filtered to give a white solid. The solid was dissolved in THF (200 mL) and DBU (1.6 mL, 10.5 mmol) was added. After 1 h, the solvent was removed in vacuo and the residue was partitioned between hexane and saturated aqueous NH4Cl. The aqueous phase was basified with solid Na2CO3, and then extracted with EtOAc (100 ml*2). The combined ethyl acetate phases was dried over MgSO4, filtered and concentrated to give compound 2 as a white solid.

1. customThe solvent was removed in vacuo and ethanol (10 ml)
2. additionwas added
3. stirringstirred for 15 min
4. filtrationfiltered
5. customto give a white solid
6. waitAfter 1 h
7. customthe solvent was removed in vacuo
8. customthe residue was partitioned between hexane and saturated aqueous NH4Cl
9. extractionextracted with EtOAc (100 ml*2)
10. dry with materialThe combined ethyl acetate phases was dried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated

ORD-Eintrag

ord-ab571e7b828c4f9999de9c14ba39e377

Quelldatensatz

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09353104B2