Реакция #91817

Уравнение реакции

( i )

2-(4-Chlorophenyl)-5-cyclopropyl-N-methyl-6-[(methylsulfonyl) (pent-4-en-1-yl)amino]-2H-indazole-3-carboxamide

acetic acid

NBS

NaOH

→

( ii )

Выход 118.7%

2-(4-chlorophenyl)-5-cyclopropyl-N-methyl-6-{(methylsulfonyl)[3-(oxiran-2-yl)propyl]amino}-2H-indazole-3-carboxamide

Выход 118.7%

Растворители

1,4-dioxane

water

water

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added
2. 2
   Экстракцияextracted with EtOAc (3×10 mL)
3. 3
   Сушкаthe combined organics then dried (MgSO4)
4. 4
   Концентрированиеconcentrated in vacuo

Методика

To a solution of (i) (156 mg, 0.32 mmol) and acetic acid (37 μL, 0.64 mmol) in anhydrous 1,4-dioxane (15 mL) and water (20 mL) at 0° C. was added NBS (68 mg, 0.13 mmol) in a single portion. The reaction mixture was allowed to warm slowly to room temperature over 1 h 25 min whereupon aq. 1M NaOH solution (3 mL) was added and the reaction followed LCMS analysis. After 30 min, the reaction mixture was diluted with water (10 mL), extracted with EtOAc (3×10 mL) and the combined organics then dried (MgSO4) and concentrated in vacuo to obtain (ii) (191 mg, >100%). The crude product was used without further purification in the next step. ESI-MS m/z calculated for [M+H]+: 503.2. found: 503.1.

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