تفاعل #713842

معادلة التفاعل

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

4-amino-2,6-dimethylpyrimidine

Xantphos

cesium carbonate

→

title compound

المردود 86.1%

[2-(2,6-Dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine-4-yl]-(2,6-dimethylpyrimidin-4-yl)amine

المردود 86.1%

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   أخرىwas sealed in a microwave vial
2. 2
   أخرىpurged with nitrogen
3. 3
   أخرىirradiated at 150° C. for 25 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 (60-80% ethyl acetate in cyclohexane)

الإجراء التجريبي

A suspension of 4-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine (200 mg, 0.57 mmol), 4-amino-2,6-dimethylpyrimidine (95 mg, 0.77 mmol), Pd2(dba)3 (16 mg, 0.018 mmol), Xantphos (39 mg, 0.067 mmol) and cesium carbonate (437 mg, 1.34 mmol) in dioxane (5 mL) was sealed in a microwave vial, purged with nitrogen and irradiated at 150° C. for 25 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 (60-80% ethyl acetate in cyclohexane) to afford the title compound as a yellow solid (189 mg, 73% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.52 (br s, 1H), 9.16 (s, 1H), 8.34 (s, 1H), 7.99 (d, J=6.4 Hz, 1H), 7.83 (d, J=1.0 Hz, 1H), 7.81 (s, 1H), 7.71 (dd, J=9.0, 7.3 Hz, 1H), 7.21 (d, J=6.4 Hz, 1H), 3.32 (s, 3H), 2.41 (s, 3H). LCMS (Method B): RT=2.93 min, m/z: 385 [M+H+].

المصدر