[4-chloro-2-(trifluoromethyl)phenyl]methanamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared following the same general protocol as described in Step 8-9, Example 1, using the (4-chloro-2-(trifluoromethyl)phenyl)methanamine and the 1-((2′-(tert-butoxycarbonyl)-[1,1′-biphenyl]-4-yl)methyl)-2,3-dimethyl-1H-indole-5-carboxylic acid. ESI-MS (m/z): 591 [M+H]+.

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Commercially available 4-chloro-2-trifluoromethylbenzylamine (1 g, 4.77 mmol) was dissolved in 20 ml of AcOEt and at 0° C. triphosgene (1.41 g, 4.77 mmol) was added to the solution. The mixture was warmed at 80° C. for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (5 ml) of compound 1b (475 mg, 3.2 mmol) and the mixture was warmed at 80° C. for 8 hours. (TLC AcOEt 4/petroleum ether 6). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1×20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 120 mg of a white solid. Yield=9.7% 1HNMR (DMSO, 200 MHz) δ 4.45 (2H, d, J=5.6 Hz), 6.99 (4H, m), 7.65 (1H, d), 7.73 (1H, d), 7.85 (1H, bs), 8.62 (1H, bs), 11.04 (1H, bs); [M+1] 386.6 (C16H11ClF3N3O3 requires 385.73). was added to the solution then evaporated the residue was dissolved in 5 ml of DMF the mixture was warmed at 80° C. for 8 hours The solvent was evaporated the crude was dissolved in AcOEt (30 ml) washed with water (1×20 ml) and brine The organic phase was dried over sodium sulfate concentrated under vacuum The purification of the crude residue by chromatographic column