تفاعل #969343

معادلة التفاعل

sodium carbonate

2-methyl-N-[3-[5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-7-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]phenyl]prop-2-enamide

2-bromopyridine

→

N-(3-(5-(pyridin-2-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)phenyl)methacrylamide

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةbefore being cooled
2. 2
   استخلاصextracted with ethyl acetate (×3)
3. 3
   غسيلwashed with brine
4. 4
   تجفيفdried with anhydrous sodium sulfate
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىThe reaction was then purified by chromatography
8. 8
   غسيلeluting with 0-100% EtOAc/petroleum ether
9. 9
   أخرىThe product was collected
10. 10
    تركيزconcentrated in vacuo

الإجراء التجريبي

To a solution of 2-methyl-N-[3-[5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-7-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]phenyl]prop-2-enamide (200 mg, 0.370 mmol) in N,N-dimethylformamide (3.0 mL) under nitrogen, was added Pd(dppf)Cl2CH2Cl2 (16 mg, 0.020 mmol), 2-bromopyridine (60 mg, 0.38 mmol), and a solution of sodium carbonate (120 mg, 1.13 mmol in water, 1 mL). The resulting solution was stirred for 2 hours at 80° C. before being cooled and extracted with ethyl acetate (×3). The organic layers were combined, washed with brine, dried with anhydrous sodium sulfate, filtered and concentrated in vacuo. The reaction was then purified by chromatography using silica gel, eluting with 0-100% EtOAc/petroleum ether. The product was collected and concentrated in vacuo to afford N-(3-(5-(pyridin-2-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)phenyl)methacrylamide as a yellow oil. LRMS (ESI) calc'd for C27H32N5O2Si [M+H]+: 486, found 486.

المصدر