Reaktion #694337

Reaktionsgleichung

product

4-Chloro-2-methyl-2H-pyrazolo[3,4-b]pyridine

product

N-[4-(2-Amino-4-methyl-phenylsulfanyl)-phenyl]-acetamide

sodium t-butoxide

→

title compound

Ausbeute 17.1%

N-{4-[4-Methyl-2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-4-ylamino)-phenylsulfanyl]-phenyl}-acetamide

Ausbeute 17.1%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITleft under a positive pressure of nitrogen
2. 2
   Temperaturheated
3. 3
   Temperaturunder reflux for 2 h
4. 4
   Temperaturwas heated
5. 5
   Temperaturunder reflux for an addition 2 h
6. 6
   Sonstigepartitioned between ethyl acetate (30 mL) and water (30 mL)
7. 7
   ExtraktionThe aqueous phase was extracted with ethyl acetate
8. 8
   Trocknenthe combined organic phase was dried over anhydrous magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    Sonstigeevaporated under reduced pressure
11. 11
    SonstigeThe residue was purified by chromatography on silica gel
12. 12
    Wascheneluting with 5% MeOH/CH2Cl2

Vorschrift

A mixture of the product of Example 8c (47.3 mg, 0.282 mmol), the product of Example 7b (84.6 mg, 0.310 mmol), Pd2(dba)3 (12.9 mg, 0.0141 mmol), sodium t-butoxide (67.8 mg, 0.706 mmol), and 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicycl[3,3,3]undecane (19.3 mg, 0.0564 mmol) in toluene (4 mL) was degassed, left under a positive pressure of nitrogen, and heated under reflux for 2 h. Additional amounts of Pd2(dba)3 (4.0 mg, 0.0044 mmol) and PN3 (4.5 mg, 0.013 mmol) were added the reaction mixture was heated under reflux for an addition 2 h. The mixture was then cooled to room temperature and partitioned between ethyl acetate (30 mL) and water (30 mL). The aqueous phase was extracted with ethyl acetate and the combined organic phase was dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with 5% MeOH/CH2Cl2, to provide the title compound (0.0195 g, 17% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.03 (s, 3H), 2.29 (s, 3H), 4.11 (s, 3H), 5.97 (d, J=5.15 Hz, 1H), 6.94-7.00 (m, 1H), 7.05 (dd, J=8.09, 1.47 Hz, 1H), 7.19 (s, 1H), 7.26 (d, J=8.82 Hz, 2H), 7.56 (d, J=8.82 Hz, 2H), 8.09 (d, J=5.15 Hz, 1H), 8.20 (s, 1H), 8.80 (s, 1H), 10.04 (s, 1H); MS (ESI+) m/z 404.1 (M+H)+.

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