تفاعل #713860

معادلة التفاعل

Sodium hydride

2-amino-4-cyanopyridine

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

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title compound

المردود 10.2%

6-[2-(2-Chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-ylamino]isonicotinonitrile

المردود 10.2%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىthe vial was sealed
2. 2
   أخرىpurged with nitrogen
3. 3
   أخرىirradiated at 150° C. for 10 minutes in the microwave
4. 4
   درجة الحرارةThe reaction mixture was cooled
5. 5
   أخرىpartitioned between ethyl acetate and water
6. 6
   غسيلThe organic layer was washed with brine
7. 7
   تجفيفdried over anhydrous sodium sulfate
8. 8
   تركيزconcentrated under reduced pressure
9. 9
   أخرىThe residue was purified by silica gel flash chromatography (50% ethyl acetate in cyclohexane)

الإجراء التجريبي

Sodium hydride (12 mg, 0.30 mmol) was added to a solution of 2-amino-4-cyanopyridine (36 mg, 0.30 mmol) in DMF (2 mL) in a microwave vial and stirred for 5 minutes. 4-Chloro-2-(2-chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine (76 mg, 0.27 mmol) was added and then the vial was sealed, purged with nitrogen and irradiated at 150° C. for 10 minutes in the microwave. 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 (50% ethyl acetate in cyclohexane) to afford the title compound as a yellow solid (10 mg, 10% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.61 (s, 1H), 8.77 (dd, J=5.2, 0.9 Hz, 1H), 7.99 (d, J=7.3 Hz, 1H), 7.85 (s, 1H), 7.81-7.80 (m, 2H), 7.73 (d, J=8.2 Hz, 1H), 7.67 (t, J=9.0 Hz, 1H), 7.58 (dd, J=7.3, 0.9 Hz, 1H). LCMS (Method B): RT=2.98 min, m/z: 365 [M+H+].

المصدر