Potassium Carbonate → 6-(6-methoxypyridin-3-yl)-1-methyl-4-(4-(methylsulfonyl)phenoxy)-1H-pyrazolo[3,4-b]pyridine

HRID 241970Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[N:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=2)[N:5]=[C:4]2[N:16]([CH3:19])[N:17]=[CH:18][C:3]=12.[CH3:20][S:21]([C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)(=[O:23])=[O:22].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:15][O:14][C:11]1[N:10]=[CH:9][C:8]([C:6]2[N:5]=[C:4]3[N:16]([CH3:19])[N:17]=[CH:18][C:3]3=[C:2]([O:30][C:27]3[CH:26]=[CH:25][C:24]([S:21]([CH3:20])(=[O:23])=[O:22])=[CH:29][CH:28]=3)[CH:7]=2)=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To 4-chloro-6-(6-methoxypyridin-3-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridine (0.32 g) and 4-(methylsulfonyl)phenol (0.40 g) in DMF (6 mL) was added potassium carbonate (0.80 g) and nitrogen was bubbled through the solution for 5 min. The reaction mixture was then heated in a microwave reactor at 150° C. for 1 h. The resulting product was purified by silica gel chromatography (0-30% EtOAc in hexane) to afford 117 (0.38 g). MS (ESI) m/z 411.1 (M+1)+

Workup

customwas bubbled through the solution for 5 min
customThe resulting product was purified by silica gel chromatography (0-30% EtOAc in hexane)

Sources & evidence

ORD record: ord-12c7531b9a4047d3880b866a1356fb52
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653098B2

Reaction notes

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