3-Methoxyphenol → HCID 46220333, compound

HRID 241961Notes

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][O:22][C:23]1[CH:24]=[C:25]([OH:29])[CH:26]=[CH:27][CH:28]=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:29][C:25]4[CH:26]=[CH:27][CH:28]=[C:23]([O:22][CH3:21])[CH:24]=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. 3-Methoxyphenol 8e (0.033 g, 0.282 mmol) was added followed by the addition of potassium carbonate (0.2 g, 1.41 mmol). Nitrogen was bubbled through the resultant reaction mixture and 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 the desired product which was to obtain 107 as a white solid (15.0 mg, 30%)

Workup

customNitrogen was bubbled through the resultant
customreaction 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-3eda577cfa0542f7aaff380102d20ee9
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653098B2

Reaction notes

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