Sodium Carbonate → N-(3-(trifluoromethyl)benzyl)-2-(2-amino-5-chlorophenyl)-isonicotinamide

Temperatur

85 °C

Into a 50-mL round bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 4-chloro-2-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)benzenamine (300 mg, 1.17 mmol, 1.00 equiv) in ethylene glycol dimethyl ether (15 mL), N-(3-(trifluoromethyl)benzyl)-2-bromoisonicotinamide (432 mg, 1.20 mmol, 1.00 equiv), a solution of sodium carbonate (636 mg, 6.00 mmol, 5.00 equiv) in water (3.0 mL), and Pd(PPh3)4 (138 mg, 0.12 mmol, 0.10 equiv). The resulting solution was stirred for 2 h at 85° C. in an oil bath. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with 10 mL of water. The resulting solution was extracted with 3×10 mL of ethyl acetate and the organic layers combined, and washed with brine. The mixture was dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with petroleum ether/ethyl acetate (10:1-5:1). The product was obtained as 260 mg (55%) of a yellow solid.

1. customInto a 50-mL round bottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. concentrationThe resulting mixture was concentrated under vacuum
4. additionThe resulting solution was diluted with 10 mL of water
5. extractionThe resulting solution was extracted with 3×10 mL of ethyl acetate
6. washwashed with brine
7. dry with materialThe mixture was dried over sodium sulfate
8. concentrationconcentrated under vacuum
9. washeluted with petroleum ether/ethyl acetate (10:1-5:1)

ORD-Eintrag

ord-8ffdf5bd6bc54ea786db3d417ff4b708

Quelldatensatz

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09301951B2