tert-butyl 5-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-fluorophenyl)-3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate → N-(5-(3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-fluorophenyl)methanesulfonamide

Participants

Reaction Steps

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 5-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-fluorophenyl)-3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (88 mg, 0.121 mmol) was deprotected in HCl in dioxane/MeOH (5/2 ml). This afforded 27 mg (35% yield) of the titled compound. 1H NMR (CDCl3, 300 MHz): δ 13.6 (s, 1H), 8.42 (s, 1H), 8.26 (s, 1H), 7.80-7.77 (d, 1H), 7.50 (s, 1H), 7.33-7.32 (m, 2H), 6.79-6.69 (m, 4H), 5.33 (s, 2H), 3.09 (s, 3H), 2.24 (s, 3H), 2.18 (s, 3H). MS: m/z=526.2 (M+1), HPLC: 94.82% in method B.

Provenance & Evidence