Ammonia → HCID 57908201, compound

A mixture of 5-chloro-2,3-difluoro-4-(1H-pyrazol-1-yl)pyridine (37 g, 0.17 mol, 1.0 equiv) and NMP (200 mL) in a pressure vessel was stirred at 50° C. under 20 psi of ammonia gas overnight. The mixture was diluted with water (400 mL) and extracted with EtOAc (2×300 mL). The organic fractions were combined, dried over Na2SO4, and concentrated under vacuum. To the residue was added water (300 mL) with stirring. The resulting solid was collected by filtration, and the cake was washed with isopropanol (100 mL) and dried under vacuum to give the desired product (24 g) as a yellow solid. The solid was recrystallized from isopropanol (40 mL) and EtOAc (20 mL) to give 19 g of pure product as an off white solid. The mother liquors were concentrated under vacuum and recrystallized from isopropanol (30 mL) to give another 5.1 g for a combined total of 24 g (67%) of desired product as an off white solid.

1. extractionextracted with EtOAc (2×300 mL)
2. dry with materialdried over Na2SO4
3. concentrationconcentrated under vacuum
4. additionTo the residue was added water (300 mL)
5. filtrationThe resulting solid was collected by filtration
6. washthe cake was washed with isopropanol (100 mL)
7. customdried under vacuum

ORD record

ord-ca97e4460be149789525d19e42015c20

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989469B2