تفاعل #713843

معادلة التفاعل

Sodium hydride

6-amino-3-pyridinecarbonitrile

4-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine

→

title compound

المردود 52.0%

6-[2-(2,6-Dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-ylamino]nicotinonitrile

المردود 52.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   أخرىThe reaction
3. 3
   أخرىvial was sealed
4. 4
   أخرىpurged with nitrogen
5. 5
   أخرىirradiated in a microwave at 150° C. for 10 minutes
6. 6
   درجة الحرارةThe reaction mixture was cooled
7. 7
   أخرىpartitioned between ethyl acetate and water
8. 8
   غسيلThe organic layer was washed with brine
9. 9
   تجفيفdried over anhydrous sodium sulfate
10. 10
    تركيزconcentrated under reduced pressure
11. 11
    أخرىThe residue was purified by silica gel flash chromatography (40% ethyl acetate in cyclohexane)

الإجراء التجريبي

Sodium hydride (12 mg, 0.30 mmol) was added to a solution of 6-amino-3-pyridinecarbonitrile (36 mg, 0.30 mmol) in DMF (2 mL) and the resultant mixture was stirred for 5 minutes before 4-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine (80 mg, 0.27 mmol) was added. The reaction vial was sealed, purged with nitrogen and irradiated in a microwave at 150° C. for 10 minutes. The reaction mixture was cooled and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (40% ethyl acetate in cyclohexane) to afford the title compound as a yellow solid (53 mg, 52% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.57 (d, J=0.9 Hz, 1H), 8.98 (dd, J=2.3, 0.8 Hz, 1H), 8.47 (dd, J=8.7, 2.3 Hz, 1H), 8.04 (d, J=7.3 Hz, 1H), 7.89-7.83 (m, 2H), 7.77 (dd, J=9.1, 7.2 Hz, 1H), 7.65-7.61 (m, 2H). LCMS (Method B): RT=3.05 min, m/z: 381 [M+H+].

المصدر