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

HRID 2070020Notes

Reaction equation

C(OC[N:10]1[C:14]2=[N:15][CH:16]=[CH:17][C:18]([O:19][C:20]3[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=3)=[C:13]2[CH:12]=[N:11]1)C1C=CC=CC=1>CO.Cl.[C].[Pd]>[NH:10]1[C:14]2=[N:15][CH:16]=[CH:17][C:18]([O:19][C:20]3[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=3)=[C:13]2[CH:12]=[N:11]1

Participants

Conditions

Temperature: 50 °C

Procedure

4-(1-Benzyloxymethyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)aniline (140 mg, 0.40 mmol) was dissolved in methanol (5 mL) and 5 N hydrochloric acid (0.2 mL), and palladium carbon (10%, 10 mg) was added thereto. The resulting mixture was stirred at 50° C. for 4 hours under a hydrogen atmosphere. The catalyst was removed by filtration, and the methanol solution was concentrated. The residue was neutralized with a 5 N sodium hydroxide aqueous solution (0.2 mL) and partitioned between saturated brine (3 mL) and ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated. The residue was purified by amino-silica gel (Fuji Silysia, 5 g, ethyl acetate) to give 4-(1H-pyrazolo[3,4-b]pyridin-4-yloxy)aniline (23 mg, yield: 25%).

Workup

customThe catalyst was removed by filtration
concentrationthe methanol solution was concentrated
custompartitioned between saturated brine (3 mL) and ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated
customThe residue was purified by amino-silica gel (Fuji Silysia, 5 g, ethyl acetate)

Sources & evidence

ORD record: ord-864386531d6748eea330dadf30c43f18
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299252B2

Reaction notes

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