Реакция #57149

Уравнение реакции

N-phenyl-N′-{4-[1-(2-propen-1-yl)-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]phenyl}urea

acetone

water

N-methylmorpholine N-oxide

→

title compound

Выход 14.0%

N-{4-[1-(2,3-dihydroxypropyl)-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]phenyl}-N′-phenylurea

Выход 14.0%

Растворители

t-butanol

Условия реакции

Обработка

1. 1
   ДругоеThe reaction was quenched with saturated aqueous sodium sulfate (11 mL)
2. 2
   Фильтрацияfiltered through a pad of celite (rinsing with ethyl acetate)
3. 3
   Концентрированиеconcentrated in vacuo
4. 4
   ДругоеThe residue was purified by Gilson reverse phase HPLC

Методика

To a solution of N-phenyl-N′-{4-[1-(2-propen-1-yl)-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]phenyl}urea (0.18 mmol) in 5:1 acetone:water (1.2 mL) was added N-methylmorpholine N-oxide (0.276 mmol) followed by a 2.5% solution of osmium tetroxide in t-butanol (93.5 mg). The reaction mixture was stirred at room temperature for 18 h. The reaction was quenched with saturated aqueous sodium sulfate (11 mL), filtered through a pad of celite (rinsing with ethyl acetate) and concentrated in vacuo. The residue was purified by Gilson reverse phase HPLC to afford the title compound as a white solid (14%). ESMS [M+H]+: 469.2

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