4-[1-(4-Methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy]aniline → 4-(1H-pyrazolo[3,4-b]pyridin-4-yloxy)aniline

HRID 2070026Notes

Reaction equation

COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=4)=[C:11]3[CH:10]=[N:9]2)=CC=1>C(O)(C(F)(F)F)=O>[NH:8]1[C:12]2=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]3[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=3)=[C:11]2[CH:10]=[N:9]1

Participants

Conditions

Temperature: 60 °C

Procedure

4-[1-(4-Methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy]aniline (263 mg) was dissolved in TFA (7.5 mL). The resulting mixture was stirred at 60° C. for 2 hours and concentrated under reduced pressure. The residue was diluted with dichloromethane and then washed with a sodium bicarbonate solution and saturated brine. The organic layer was separated and concentrated under reduced pressure. The residue was suspended in ether, and the precipitate was collected by filtration to give 4-(1H-pyrazolo[3,4-b]pyridin-4-yloxy)aniline (151 mg, yield: 88%) as a light-brown powder.

Workup

concentrationconcentrated under reduced pressure
additionThe residue was diluted with dichloromethane
washwashed with a sodium bicarbonate solution and saturated brine
customThe organic layer was separated
concentrationconcentrated under reduced pressure
filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record: ord-83cd822d725c415caa649f5eb6e79c20
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299252B2

Reaction notes

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