Triethylamine → HCID 57501775, compound

Participants

Reaction Steps

Dissolve 2-(4-chloro-phenyl)-4-(2-hydroxy-ethyl)-thiazole-5-carboxylic acid (1-triisopropylsilanyl-1H-indol-5-yl)-amide in CH2Cl2 (25 mL) and add Et3N (0.33 mL, 2.36 mmol) and methanesulfonyl chloride (0.16 mmol, 2.13 mmol). Stir the mixture at room temperature for 2 h, then add additional Et3N (0.33 mL, 2.36 mmol) and methanesulfonyl chloride (0.16 mmol, 2.13 mmol). Stir the mixture for an additional 2 h, dilute with EtOAc (50 mL), then wash with water (20 mL) and brine (20 mL). Dry, filter and concentrate the organic solution then and purify the crude material by flash chromatography, using a linear gradient of 100% hexanes to 50% EtOAc/hexanes as eluent, to give the title compound (1.15 g, 100%). MS (ES+) 536.1 (M+1)+. 1H NMR (400 MHz, CDCl3) δ: 7.93 (d, 2H, J=8.3 Hz), 7.56 (d, 1H, J=1.8 Hz), 7.50 (d, 1H, J=8.8 Hz), 7.44 (d, 2H, J=8.3 Hz), 7.27 (d, 1H, J=3.1 Hz), 7.14-7.10 (m, 1H), 6.61 (d, 1H, J=2.6 Hz), 4.16 (t, 2H, J=6.8 Hz), 3.29 (t, 2H, J=7.0 Hz), 1.73-1.65 (m, 3H), 1.14 (d, 18H, J=7.5 Hz).

Provenance & Evidence