Dimethylacetamide → 3-Cyano-5-nitro-2'-trifluoromethyl-biphenyl-4-ylamine

Temperature

140 °C

The title compound was prepared by an adaptation of the method described by Youngblood, W. J. (J. Org. Chem. 2006, 71, 3345-3356). 3-Iodo-5-nitro-2′-trifluoromethyl-biphenyl-4-ylamine (230 mg, 0.564 mmol, as prepared in the previous step) and Cu(I)CN (1.5 eq., 7.57 mg, 0.845 mmol) were placed in an 8 mL vial equipped with a magnetic stir bar. Dry DMA (2.5 mL) was added via syringe, and the vial was tightly capped and placed in a heating block. The reaction was stirred at 140° C. for 14 h, cooled to RT, and poured into water. The precipitate was isolated by filtration and washed with water (10 mL). The precipitate was dissolved in EtOAc (25 mL), dried over anhydrous MgSO4, filtered, and the solvent was removed under reduced pressure. The crude product was purified by preparative TLC on a 2000 μm SiO2 plate developed with EtOAc/hexanes, 1:9 v/v, yielding 86 mg (50%) of the title compound. 1H-NMR (400 MHz, CDCl3) δ: 8.37 (d, J=1.8 Hz, 1H), 7.79 (d, J=7.8 Hz, 1H), 7.71 (d, J=1.5 Hz, 1H), 7.62 (t, J=7.3 Hz, 1H), 7.55 (t, J=7.7 Hz, 1H), 7.31 (d, J=7.6 Hz, 1H), 6.84 (br. s., 2H).

1. customThe title compound was prepared by an adaptation of the method
2. customvial equipped with a magnetic stir bar
3. customthe vial was tightly capped
4. temperaturecooled to RT
5. customThe precipitate was isolated by filtration
6. washwashed with water (10 mL)
7. dissolutionThe precipitate was dissolved in EtOAc (25 mL)
8. dry with materialdried over anhydrous MgSO4
9. filtrationfiltered
10. customthe solvent was removed under reduced pressure
11. customThe crude product was purified by preparative TLC on a 2000 μm SiO2 plate

ORD record

ord-ebc4366dda694f8abed1330cf0736d1a

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08232409B2