Sodium Hydroxide → 3-bromo-1-isopropyl-6-(4-(morpholinomethyl)phenyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 1854005Notes

Reaction equation

[Br:1][C:2]1[C:10]2[C:9]([C:11]([O:13]CC)=[O:12])=[CH:8][C:7]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:18][CH:17]=3)=[N:6][C:5]=2[N:4]([CH:29]([CH3:31])[CH3:30])[N:3]=1.[OH-].[Na+]>CCO>[Br:1][C:2]1[C:10]2[C:9]([C:11]([OH:13])=[O:12])=[CH:8][C:7]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)=[CH:18][CH:17]=3)=[N:6][C:5]=2[N:4]([CH:29]([CH3:31])[CH3:30])[N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 3-bromo-1-isopropyl-6-(4-(morpholinomethyl)phenyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (1 g, 2.05 mmol) in EtOH (15 mL), aqueous NaOH (0.123 g, 3.08 mmol) was added and reaction mixture stirred at 60° C. for 1 h. After completion of the reaction, ethanol was removed under reduced pressure and it was acidified using 10% citric acid solution. Solid obtained was filtered and azeotrope it with toluene to give the desired compound (0.8 g, 84.9%).

Workup

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customwas removed under reduced pressure and it
customSolid obtained
filtrationwas filtered

Sources & evidence

ORD record: ord-0c4082efef474c00ba6e29bfc1d04e9c
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962620B2

Reaction notes

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