Hydrochloric Acid → 5-cyclopropyl-2-(4-hydroxyphenyl)-6-[(3-hydroxypropyl)(methylsulfonyl)amino]-N-methyl-2H-indazole-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

2-(4-Bromophenyl)-5-cyclopropyl-6-[(3-hydroxypropyl)(methylsulfonyl)amino]-N-methyl-2H-indazole-3-carboxamide (i) (16 mg, 0.031 mmol) in 1,4-dioxane (0.5 mL) had a solution of potassium hydroxide (9 mg, 0.016 mmol) in water (0.5 mL) added and was degassed. tert-Butyl-XPhos (4 mg, 0.009 mmol) and Pd2(dba)3 (4 mg, 0.004 mmol) were added and the reaction was heated at 100° C. for 4 h. The mixture was cooled to RT, 1 M hydrochloric acid (0.5 mL) was added and this was then concentrated to dryness. The residue was purified by reverse phase flash column chromatography eluting with ACN/water (5-100%) to afford 5-cyclopropyl-2-(4-hydroxyphenyl)-6-[(3-hydroxypropyl)(methylsulfonyl)amino]-N-methyl-2H-indazole-3-carboxamide (ii) as a white solid (8 mg, 57%).

Provenance & Evidence