Ammonium Chloride → HCID 66869519, compound

Participants

Reaction Steps

Sodium tert-butoxide (354 mg, 3.68 mmol) is dried under high vacuum at approximately 80° C. After purging with argon and cooling to RT, palladium acetate (60 mg, 0.27 mmol), rac-2,2′-bis-diphenylphosphanyl-[1,1]binaphthalenyl (rac-BINAP, 83 mg, 0.13 mmol) and (2-chloro-5-trifluoromethyl-pyridin-4-yl)-acetic acid tert-butyl ester (990 mg, 3.35 mmol) are added. The mixture is dissolved in dioxane (11 ml, degassed with three freeze-thaw cycles under HV/argon), and 1-methyl-piperazine (369 mg, 3.68 mmol) is added. The round bottom flask containing the reaction mixture is immersed into a pre-heated oil bath (T=85° C.). After 1 h, TLC analysis indicated almost complete conversion of starting materials. The reaction mixture is cooled to RT, diluted with EtOAc and poured into a saturated aqueous NH4Cl solution. The organic layer is separated, washed with brine, dried over Na2SO4, and the solvent is evaporated. The residue is purified by FCC (CH2Cl2/MeOH, slow gradient from 99:1 to 94:6) to afford the title compound. 1H NMR (CDCl3, 400 MHz): δ 1.44 (s, 9H), 2.34 (s, 3H), 2.50 (m, 4H), 3.59 (s, 2H), 3.66 (m, 4H), 6.54 (s, 1H), 8.35 (s, 1H). ES+−MS: 360.3 [M+H]+.

Provenance & Evidence