2,6-Dimethylphenol → 4-(2,6-dimethylphenoxy)-6-(1H-indazol-4-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridine

HRID 241960Notes

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][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:23]=1[OH:29].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH3:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:23]=1[O:29][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

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 mmol) was dissolved in 2 mL DMF. 2,6-Dimethylphenol 8b (0.034 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 30 minutes. 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 and solvent removed and purified to obtain 106 as a white solid (10 mg, 20%). 1H NMR (400 MHz, CDCl3) δ 10.13 (s, 1H), 8.77 (s, 1H), 7.58 (t, J=7.2, 2H), 7.48 (dd, J=11.8, 19.0, 2H), 7.18 (s, 3H), 6.97 (d, J=23.8, 1H), 4.22 (s, 3H), 2.19 (s, 6H)

Workup

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

Sources & evidence

ORD record: ord-d43b5b18bdc645239ebd6f756b575380
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653098B2

Reaction notes

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