2-Dimethylaminopyridine → HCID 22676818, compound

Participants

Reaction Conditions

Reaction Steps

Triflic anhydride (0.84 mL, 1.4 g, 5.0 mmol) and dimethylaminopyridine (25 mg, 0.20 mmol) were added to a cooled (0° C.) and stirred solution of ethyl 3-[3-(cyclopropylmethoxy)phenyl]-5-hydroxy-1-(3-methoxybenzyl)-1H-indole-2-carboxylate (Example 66, 1.00 g, 2.12 mmol) in dichloromethane (10 mL) and pyridine (2 mL). The reaction was warmed to rt and then stirred an additional 2 h. The solution was diluted with ethyl acetate (100 mL), washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. Flash chromatography of the residue over silica gel using 15% ethyl acetate/hexane afforded 1.14 g (89%) of desired product. The product had: 1H NMR (300 MHz, acetone-D6) δ 7.73 (d, 1 H), 7.54 (d, 1 H), 7.35-7.42 (m, 3 H), 7.20 (dd, 1 H), 7.00-7.07 (m, 2 H), 6.68-6.83 (m, 3 H), 5.88 (s, 2 H), 4.16 (q, 2 H), 3.91 (d, 2 H), 3.72 (s, 3 H), 1.25-1.35 (m, 1 H), 10.5 (t, 3 H), 0.55-0.65 (m, 2 H), 0.32-0.42 (m, 2 H); mass spectroscopy gave M+=603.1 (exact mass calc'd for C20H28F3NO7S=603.15).

Provenance & Evidence