تفاعل #680036

معادلة التفاعل

201a

5-Bromo-3-(imidazo[1,2-a]pyridin-7-ylamino)-1-methylpyrazin-2(1H)-one

{3-[(acetyloxy)methyl]-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridin-4-yl}boronic acid

{3-[(Acetyloxy)methyl]-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridin-4-yl}boronic Acid

K3PO4

acetonitrile

→

201b

المردود 34.0%

(2-{4,4-Dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}-4-[6-({imidazo[1,2-a]pyridin-6-yl}amino)-4-methyl-5-oxo-4,5-dihydropyrazin-2-yl]pyridin-3-yl)methyl Acetate

المردود 34.0%

ظروف التفاعل

المعالجة

1. 1
   أخرىA 25-mL single-neck round-bottomed flask equipped with a reflux condenser
2. 2
   أخرىThe system was evacuated
3. 3
   workup.ADDITIONrefilled with N2
4. 4
   درجة الحرارةIt was then cooled to room temperature
5. 5
   ترشيحfiltered
6. 6
   تركيزThe filtrate was concentrated under reduced pressure
7. 7
   أخرىthe resulting residue was purified by silica-gel column chromatography
8. 8
   غسيلeluting with 20:1 dichloromethane/methanol

الإجراء التجريبي

A 25-mL single-neck round-bottomed flask equipped with a reflux condenser was charged with 201a (64 mg, 0.20 mmol), {3-[(acetyloxy)methyl]-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridin-4-yl}boronic acid 199e (160 mg, 0.40 mmol), Pd(dppf)Cl2 (10 mg, 0.012 mmol), K3PO4 (100 mg, 0.39 mmol), NaOAc.3H2O (60 mg, 0.44 mmol), water (6 drops), and acetonitrile (5 mL). The system was evacuated and refilled with N2. The reaction mixture was stirred at 100° C. for 2 h. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica-gel column chromatography eluting with 20:1 dichloromethane/methanol to afford 201b (40 mg, 34%) as a yellow brown solid. MS-ESI: [M+H]+ 593.2.

المصدر