To a suspension of compound (ix) (320 mg, 0.83 mmol) in DCM (20 mL) was added DIPEA (0.43 mL, 2.49 mmol) followed by methanesulfonyl chloride (0.32 mL, 4.15 mmol) and the reaction mixture was stirred at RT for 3 h (monitored by LCMS). The mixture was diluted with DCM (20 mL), washed with saturated ammonium chloride (20 mL), brine (20 mL) and dried (MgSO4). The solvent was removed in vacuo to give a yellow solid. This material was taken up in ethanol (20 mL) and treated with powdered potassium hydroxide (210 mg, 3.80 mmol) and stirred for 5 min. The mixture was neutralized by addition of 1M aqueous hydrochloric acid and the resulting suspension was concentrated in vacuo to give an orange residue. The residue was taken up in DCM (20 mL), washed with water (20 mL), dried over MgSO4 and the solvent was removed in vacuo to give 2-(4-bromophenyl)-5-cyclopropyl-N-methyl-6-[(methylsulfonyl)amino]-2H-indazole-3-carboxamide (1) (300 mg, 86%) as yellow solid. ESI-MS m/z calculated for [M+H]+: 463.04/465.04; found: 463.05/465.05. 1H NMR (400 MHz, CDCl3) δ 7.82 (d, J=0.4 Hz, 1H), 7.68 (d, J=0.5 Hz, 1H), 7.65 (brd, J=8.8 Hz, 2H), 7.47 (d, J=8.8 Hz, 2H), 7.09 (s, 1H), 5.80 (brd, J=4.1 Hz, 1H), 3.13 (s, 3H), 3.00 (d, J=4.9 Hz, 3H), 1.80 (dddd, J=13.6, 8.1, 5.4, 1.3 Hz, 1H), 1.16-0.99 (m, 2H), 0.79-0.67 (m, 2H).
