Water → 1-Ethyl-3-[4-(3H-imidazo[4,5-b]pyridin-2-yloxy)phenyl]-1H-pyrazolo[4,3-b]pyridine

HRID 573295Notes

Reaction equation

[CH2:1]([N:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[N:27](COCC[Si](C)(C)C)[C:22]4=[N:23][CH:24]=[CH:25][CH:26]=[C:21]4[N:20]=3)=[CH:14][CH:13]=2)=[N:4]1)[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[CH2:1]([N:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[NH:27][C:22]4=[N:23][CH:24]=[CH:25][CH:26]=[C:21]4[N:20]=3)=[CH:14][CH:13]=2)=[N:4]1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-ethyl-3-[4-(3-{[2-(trimethylsilyl)ethoxy]methyl}-3H-imidazo[4,5-b]pyridin-2-yloxy)phenyl]-1H-pyrazolo[4,3-b]pyridine (90 mg), 1 M TBAF in THF (0.74 mL) and THF (2 ml) was heated at 100° C. for 3 h under microwave irradiation. The mixture was stirred at 80° C. overnight. The mixture was poured into water and extracted with AcOEt. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (AcOEt/hexane) to give the title compound (18 mg).

Workup

extractionextracted with AcOEt
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by basic silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record: ord-5cb2fbe52a004876ae7166147f824a1c
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029536B2

Reaction notes

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