Methanol → (r)-n-(2-Aminoindan-5-yl)-6-methyl-4'-trifluoromethylbiphenyl-2-carboxamide

Temperature

0 °C

(R)-6-methyl-4′-trifluoromethylbiphenyl-2-carboxylic acid (2-methoxycarbonylaminoindan-5-yl)-amide (6.5 g, 13.9 mmol) is dissolved in acetonitrile (325 mL) and cooled to 0° C. under nitrogen. Iodotrimethylsilane (11.1 g, 55.6 mmol) is added dropwise, the mixture is allowed to warm to room temperature and is stirred overnight. Methanol (100 mL) is added and the mixture is stirred for 1 hour and then concentrated in vacuo. The residue is dissolved in ethyl acetate (750 mL) and washed with saturated sodium bicarbonate (2×125 mL), water (125 mL), 5% Na2S2O3 solution (125 mL), water (125 mL), and brine (50 mL). The organic phase is dried over sodium sulfate and concentrated to afford (R)-N-(2-aminoindan-5-yl)-6-methyl-4′-trifluoromethylbiphenyl-2-carboxamide.

1. temperatureto warm to room temperature
2. stirringthe mixture is stirred for 1 hour
3. concentrationconcentrated in vacuo
4. dissolutionThe residue is dissolved in ethyl acetate (750 mL)
5. washwashed with saturated sodium bicarbonate (2×125 mL), water (125 mL), 5% Na2S2O3 solution (125 mL), water (125 mL), and brine (50 mL)
6. dry with materialThe organic phase is dried over sodium sulfate
7. concentrationconcentrated

ORD record

ord-83a6e129983c47cb8a982d0ea0105919

Source dataset

uspto-grants-2001_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06197798B1