HCID 59192802, compound → HCID 59192802, compound

Participants

Reaction Conditions

Reaction Steps

3-(5-Methylisoxazol-3-yl)-2,2-bis(3-(trifluoromethoxy)phenyl)-propanenitrile (476 mg, 94% yield) was prepared as described in Example 10 (Procedure 13 and 14). LCMS: RT=2.05 min [M+H] 456.97 (2 min Phenomenex Luna C18 column, 4.6×30 mm eluting with 10-90% MeOH/H2O over 2 minutes containing 0.1% TFA; 5 mL/min, monitoring at 220 nm); HPLC: RT=4.113 min (Phenomenex Luna C18 column, 4.6×50 mm eluting with 10-90% MeOH/H2O over 4 minutes containing 0.2% PPA; 4 mL/min, monitoring at 220 nm). To a solution of 3-(5-methylisoxazol-3-yl)-2,2-bis(3-(trifluoromethoxy)phenyl)propanenitrile (0.172 g, 3.77 mmol) in THF was added BH3 (1.0 M in THF, 1.5 ml, 9.05 mmol) and the reaction was heated at 70° C. for 2 h. The reaction mixture was quenched with 1N HCl and the pH was adjusted to pH>10 by addition of 4N NaOH. The aqueous portion was extracted with EtOAc (3×30 mL). The combined organic portions were washed with water, sat. NaCl, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to yield 3-(5-methylisoxazol-3-yl)-2,2-bis(3-(trifluoromethoxy)phenyl)propan-1-amine as a clear oil (112 mg, 65% yield) which was used without further purification. LCMS: RT=1.78 min [M+H] 461.1 (2 min Phenomenex Luna C18 column, 4.6×30 mm eluting with 10-90% MeOH/H2O over 2 minutes containing 0.1% TFA; 5 mL/min, monitoring at 220 nm.

Provenance & Evidence