Reaction Steps
A yellow solution of 2-(3-(6-isopropoxypyridin-2-yl)-1-tosyl-1H-indol-5-yl)-5-(methylsulfonyl)-1,3,4-thiadiazole (107.4 mg, 0.189 mmol) and (3R)-(+)-3-(tert-butoxycarbonylamino)pyrrolidine (TCI America, Portland, Oreg.; 141 mg, 0.755 mmol) in dioxane (1.0 mL) was heated in an open microwave vial at 90° C. for 2 days. Chromatographic purification of the resulting dry residue (silica gel, 0-100% EtOAc/Hex) furnished (R)-tert-butyl 1-(5-(3-(6-isopropoxypyridin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-thiadiazol-2-yl)pyrrolidin-3-ylcarbamate (95 mg, 0.141 mmol, 75%) as an off-white solid: MS (ESI, pos. ion) m/z: 675.1 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 8.78 (d, J=1.0 Hz, 1H), 8.02-8.08 (m, 2H), 7.94-7.99 (m, 1H), 7.82 (d, J=8.4 Hz, 2H), 7.61 (t, J=7.8 Hz, 1H), 7.28 (d, J=7.4 Hz, 1H), 7.24 (d, J=8.4 Hz, 2H), 6.63 (d, J=8.2 Hz, 1H), 5.57 (spt, J=6.2 Hz, 1H), 4.66-4.84 (m, 1H), 4.41 (br. s., 1H), 3.83 (dd, J=10.6, 6.1 Hz, 1H), 3.67-3.73 (m, 1H), 3.59-3.67 (m, 1H), 3.48-3.55 (m, 1H), 3.45 (dd, J=10.6, 4.1 Hz, 1H), 2.34 (s, 3H), 1.46 (s, 9H), 1.45 (br. s., 3H), 1.44 (br. s., 3H).
