Nitrogen → (R)-1-(4-(2-(3-(fluoromethyl)pyrrolidin-1-yl)ethoxy)benzyl)-2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol

Participants

Reaction Steps

A solution of (R)-5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-1-(4-(2-(3-(fluoromethyl)pyrrolidin-1-yl)ethoxy)benzyl)-3-methyl-1H-indole (263 mg, 0.40 mmol) in ethyl acetate/ethanol (4:1, 6 mL) was degassed with three vacuum/N2 cycles. To this solution was added 10% Pd on carbon (120 mg, 0.11 mmol) and then the needle of a H2 balloon was placed into the reaction flask. The mixture was stirred at room temperature for 15 hrs then diluted with ethyl acetate, filtered through Celite and concentrated. The residue was dried further on high vacuum to give 171 mg of (R)-1-(4-(2-(3-(fluoromethyl)pyrrolidin-1-yl)ethoxy)benzyl)-2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol as a beige solid. 1H NMR (400 MHz, DMSO-d6): δ 9.67 (s, 1H), 8.69 (s, 1H), 7.16 (d, 2H), 7.06 (d, 1H), 6.85 (d, 2H), 6.80 (d, 1H), 6.75 (s, 4H), 6.57 (dd, 1H), 5.10 (s, 2H), 4.35-4.30 (m, 1H), 4.23-4.18 (m, 1H), 3.94 (t, 2H), 2.70 (t, 2H), 2.62 (t, 1H), 2.56-2.40 (m, 3H), 2.38-2.31 (m, 1H), 2.10 (s, 3H), 1.87-1.76 (m, 1H), 1.40-1.31 (m, 1H). LCMS: 475.2 (M+H)+.

Provenance & Evidence