Potassium Carbonate → HCID 46220225, compound

HRID 241956Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH:10]=[N:11][NH:12]3)[N:5]=[C:4]2[N:17]([CH3:20])[N:18]=[CH:19][C:3]=12.[CH3:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1)(=[O:24])=[O:23].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH:12]1[C:13]2[C:9](=[C:8]([C:6]3[N:5]=[C:4]4[N:17]([CH3:20])[N:18]=[CH:19][C:3]4=[C:2]([O:31][C:28]4[CH:27]=[CH:26][C:25]([S:22]([CH3:21])(=[O:24])=[O:23])=[CH:30][CH:29]=4)[CH:7]=3)[CH:16]=[CH:15][CH:14]=2)[CH:10]=[N:11]1

Participants

Conditions

Temperature: 155 °C

Procedure

4-Chloro-6-(1H-indazol-4-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridine 7 (0.1 g, 0.352 m moles) was dissolved in 2 mL DMF. 4-Methylsulfonylphenol 8a (0.12 g, 0.704 mmol) and potassium carbonate (0.24 g, 1.76 mmol) were added. After bubbling nitrogen gas through the reaction mixture, it was heated by microwave at 155° C. for 1.5-2 hours. Solvent was removed, excess potassium carbonate was filtered and partitioned and extracted with ethyl acetate. The organic portions were washed with saturated sodium bicarbonate solution followed by brine, dried over anhydrous Na2SO4, solvent removed and purified to obtain 101. 1H NMR (400 MHz, DMSO) δ 13.26 (s, 1H), 8.77 (s, 1H), 8.06 (d, J=8.8, 2H), 7.92-7.51 (m, 6H), 7.51-7.27 (m, 2H), 4.13 (s, 3H), 3.28 (s, 3H) MS (ESI) m/z 420.1 (M+1)+

Workup

customAfter bubbling nitrogen gas through the reaction mixture, it
customSolvent was removed
filtrationexcess potassium carbonate was filtered
custompartitioned
extractionextracted with ethyl acetate
washThe organic portions were washed with saturated sodium bicarbonate solution
dry with materialdried over anhydrous Na2SO4, solvent
customremoved
custompurified

Sources & evidence

ORD record: ord-94e15ecbd0534303b1a7a8ffb5462300
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653098B2

Reaction notes

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