benzyl 1-benzyl-6-[4-fluoro-3-(methoxycarbonyl)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylate → 1-benzyl-6-[4-fluoro-3-(methoxycarbonyl)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 574995Notes

Reaction equation

[CH2:1]([N:8]1[C:12]2[N:13]=[C:14]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[C:29]([C:34]([O:36][CH3:37])=[O:35])[CH:28]=3)[CH:15]=[C:16]([C:17]([O:19]CC3C=CC=CC=3)=[O:18])[C:11]=2[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>S(=O)(=O)(O)O>[CH2:1]([N:8]1[C:12]2[N:13]=[C:14]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[C:29]([C:34]([O:36][CH3:37])=[O:35])[CH:28]=3)[CH:15]=[C:16]([C:17]([OH:19])=[O:18])[C:11]=2[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Benzyl 1-benzyl-6-[4-fluoro-3-(methoxycarbonyl)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (12.0 g/24.2 mmol) is dissolved in 100 mL of concentrated sulphuric acid. The solution is heated at 50° C. for 1 hour. The reaction mixture is then slowly run into ice-cold water and extracted with EtOAc. The organic phase is washed with water and then with a saturated aqueous solution of NaCl, dried over sodium sulphate and concentrated to dryness to give 6.25 g of a yellow-orange powder (yield: 82%).

Workup

extractionextracted with EtOAc
washThe organic phase is washed with water
dry with materialwith a saturated aqueous solution of NaCl, dried over sodium sulphate
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-e928d02cef5f4905bed192a18ad26d0c
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034898B2

Reaction notes

Loading…