Triethylsilane → HCID 53246500, compound

Participants

Reaction Steps

Benzyl 2-(2-methyl-3-(2-(phenylsulfonyl)benzyl)-5-(pyridin-2-yl)-1H-pyrrol-1-yl)acetate was synthesized according to general procedure I (step 1), with the exception that 6 equivalents of triethylsilane and 4.5 equivalents of trimethylsilyl trifluoromethanesulfonate were used. The crude benzyl 2-(2-methyl-3-(2-(phenylsulfonyl)benzyl)-5-(pyridin-2-yl)-1H-pyrrol-1-yl)acetate was taken forward. In a small recovery flask, H2 was flushed over a stirring solution of benzyl 2-(2-methyl-3-(2-(phenylsulfonyl)benzyl)-5-(pyridin-3-yl)-1H-pyrrol-1-yl)acetate (350 mg, 0.652 mmol), Pd/C (20 mg, 0.019 mmol) in MeOH (2 ml) followed by subjection to 1 atm (balloon) positive pressure of H2. After 1.5 hours, the reaction vial was flushed with nitrogen gas and the mixture was filtered through a 2 micron filter. The colorless mixture was concentrated to afford 2-(2-methyl-3-(2-(phenylsulfonyl)benzyl)-5-(pyridin-3-yl)-1H-pyrrol-1-yl)acetic acid (277 mg, 95%) as a fine yellow powder. 1H NMR (CDCl3/400 MHz) 11.77 (bs, 1H), 8.7 (s, 1H), 8.44 (d, 1H), 8.25 (d, 1H), 7.86-7.82 (m, 3H), 7.54-7.37 (m, 6H), 7.17 (d, 1H), 5.76 (s, 1H), 4.46 (s, 2H), 4.03 (s, 2H), 1.99 (s, 3H). MS m/z=447.4 (M+1).

Provenance & Evidence