Diisopropylethylamine → HCID 22286093, compound

Participants

Reaction Steps

To a mixture of 4-fluoro-2-(4-iodo-2-methyl-phenylamino)benzoic acid (3.32 g, 8.95 mmol) in dichloromethane at ambient temperature was added diisopropylethylamine (2.82 mL, 16.2 mmol). To the resultant solution was added O-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-hydroxylamine (2.19 g, 10.65 mmol) and PyBOP. After 1.5 h of stirring, the solution was diluted with ether (100 mL) and was washed with water (3×50 mL) and brine (50 mL), dried over magnesium sulfate and filtered, and concentrated in vacuo to obtain a gum. Chromatographed the gum using a gradient of 100% hexanes to 30% ethyl acetate in hexanes over 45 min. The solvent of the combined fractions was removed in vacuo to obtain a yellow gum. The gum was dried on a vacuum pump for c.a. 18 h which afforded N-[3-(tert-Butyl-dimethyl-silanyloxy)-propoxy]-4-fluoro-2-(4-iodo-2-methyl-phenylamino)-benzamide as a solid. (4.06 g, 81% yield). 1H-NMR (400 MHz, CDCl3) δ 9.3 (br. s., 1H), 9.0 (br. s., 1H), 7.58 (s, 1H), 7.49 (dd, 1H, J=8.3, 1.95 Hz)), 7.36 (br. t., 1H, =5.71 Hz), 7.05 (d, 1H, J=8.3 Hz), 6.65 (dd, 1H, J=11.96, 2.44 Hz), 6.4 (br. t., J=7.1 Hz), 4.14 (t, 2H, J=5.61 Hz), 3.812 (t, 2H, J=5.62 Hz), 2.28 (s, 3H), 1.94 (p, 2H, J=5.86 Hz), 0.9 (s, 9H), 0.08 (s, 6H). 19F-NMR (376 MHz, CDCl3) δ −105.25. MS (AP+) 559.2 m/z, (AP−) 557.1 m/z.

Provenance & Evidence