Triethylamine → N-[(6-chloro-5-fluoropyridin-3-yl)methyl]-2,2-difluoroethylamine

At 45° C., 520 mg (2.89 mmol) of 6-chloro-3-chloromethyl-5-fluoropyridine (Va-4), 1.05 ml (14.44 mmol) of 2,2-difluoroethylamine and 400 μl (2.89 mmol) of triethylamine in 50 ml of acetonitrile are stirred for about 48 hours. During the reaction, after about 16 hours and 32 hours, a further 0.42 ml (5.78 mmol) of 2,2-difluoroethylamine are added in each case. The reaction mixture is concentrated under reduced pressure and then taken up in 1 N aqueous hydrochloric acid and washed with ethyl acetate. The aqueous phase is made alkaline using 2.5 N aqueous sodium hydroxide solution and extracted repeatedly with ethyl acetate. Drying of the combined organic phases over sodium sulphate and concentration under reduced pressure gives 370 mg (57% of theory) of N-[(6-chloro-5-fluoropyridin-3-yl)methyl]-2,2-difluoroethylamine.

1. customDuring the reaction
2. concentrationThe reaction mixture is concentrated under reduced pressure
3. washwashed with ethyl acetate
4. extractionextracted repeatedly with ethyl acetate
5. dry with materialDrying of the combined organic phases over sodium sulphate and concentration under reduced pressure

ORD record

ord-ec5eefc20c8642a28012a98e91093136

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08138350B2