تفاعل #57210

معادلة التفاعل

tetrahydrofuryl bromide

potassium tert-butoxide

tetrahydrofuran

N-[4-(4-bromo-1H-pyrazol-3-yl)phenyl]-N′-phenylurea

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title compound

المردود 53.0%

N-{4-[4-bromo-1-(tetrahydro-2-furanylmethyl)-1H-pyrazol-3-yl]phenyl}-N′-phenylurea

المردود 53.0%

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 18 h
2. 2
   أخرىby quenching with saturated aqueous ammonium chloride (1 mL)
3. 3
   workup.ADDITIONThe reaction mixture was diluted with water (3 mL)
4. 4
   استخلاصextracted with ethyl acetate (3×5 mL)
5. 5
   تجفيفThe combined organic layers were dried over magnesium sulfate
6. 6
   تركيزconcentrated in vacuo

الإجراء التجريبي

To a solution of N-[4-(4-bromo-1H-pyrazol-3-yl)phenyl]-N′-phenylurea (0.28 mmol) in anhydrous N,N-dimethylformamide (6 mL) cooled to 0° C. was added 1.0M potassium tert-butoxide in tetrahydrofuran (1.12 mmol) dropwise. The reaction mixture was stirred for a further 15 minutes in the cold before dropwise addition of tetrahydrofuryl bromide (0.28 mmol). The reaction mixture was stirred at room temperature for 18 h, followed by quenching with saturated aqueous ammonium chloride (1 mL). The reaction mixture was diluted with water (3 mL) and extracted with ethyl acetate (3×5 mL). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. Gilson reverse phase HPLC afforded the title compound (53%). ESMS [M+H]+: 441.4

المصدر