Ammonia → HCID 21928183, compound

KF (1.95 g, 33.5 mmol) and CuI (6.40 g, 33.5 mmol) were weighed in a flask, and the mixture was heated with a gas burner while gently shaking under high vacuum until the content becomes a pale-yellow green. After cooling to room temperature, anhydrous DMF (50 ml), anhydrous THF (20 ml) and trimethyl (trifluoromethyl)silane (4.80 g, 33.5 mmol) were added. The mixture was heated to 50° C., and stirred for 21 hrs. A mixed solution of Compound 2,6-dichloro-5-iodonicotinonitrile (5.00 g, 16.7 mmol) in anhydrous DMF (10 ml) anhydrous THF (20 ml) was added dropwise to the above mentioned reaction mixture at 50° C. and stirred for 30 hrs. The reaction mixture was cooled to room temperature, poured into 12% aqueous ammonia, and the mixture was extracted EtOAc. The combined organic layer was concentrated in vacuo and the residue was purified by flash chromatography on silica to afford Compound 2,6-dichloro-5-(trifluoromethyl)nicotinonitrile. (1.5 g, yield: 37.5%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 9.12 (s, 1H).

1. temperaturethe mixture was heated with a gas burner
2. temperatureThe mixture was heated to 50° C.
3. stirringstirred for 21 hrs
4. customreaction mixture at 50° C.
5. stirringstirred for 30 hrs
6. temperatureThe reaction mixture was cooled to room temperature
7. extractionthe mixture was extracted EtOAc
8. concentrationThe combined organic layer was concentrated in vacuo
9. customthe residue was purified by flash chromatography on silica

ORD record

ord-141c219227d940efbecc86f3aca9a80b

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09145429B2