Potassium Carbonate → 4-(6-(1H-indazol-4-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)benzamide

HRID 241963Notes

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.[OH:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH2:28])=[O:27])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=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:21][C:22]4[CH:30]=[CH:29][C:25]([C:26]([NH2:28])=[O:27])=[CH:24][CH:23]=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 (0.040 g, 0.141 mmoles) was dissolved in 2 mL DMF. 4-Hydroxybenzamide 8d (0.038 g, 0.281 mmol) was added followed by the addition of potassium carbonate (0.2 g, 1.41 mmol) and the resultant reaction mixture was heated in a microwave at 155° C. for 1 hour. The reaction mixture was diluted with ethyl acetate and filtered and the organic portions were washed with saturated sodium bicarbonate solution followed by brine, dried over anhydrous sodium sulfate, solvent removed and purified to obtain 109 as a white solid (10 mg, 20%). 1H NMR (400 MHz, DMSO) δ 13.25 (s, 1H), 8.72 (s, 1H), 8.04 (d, J=8.7, 3H), 7.83-7.59 (m, 3H), 7.59-7.29 (m, 4H), 7.23 (s, 1H), 4.16 (d, J=9.1, 3H). MS (ESI) m/z 385.1 (M+1)+

Workup

customthe resultant reaction mixture
filtrationfiltered
washthe organic portions were washed with saturated sodium bicarbonate solution
dry with materialdried over anhydrous sodium sulfate, solvent
customremoved
custompurified

Sources & evidence

ORD record: ord-f8094f1a6c71461d9b843d90521217cb
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653098B2

Reaction notes

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