Ethanol → 1-(1-Methylethyl)-6-[4-(methyloxy)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 1522474Notes

Reaction equation

HRID 1522474 reaction equation
[CH3:1][CH:2]([N:4]1[C:8]2[N:9]=[C:10]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[CH:11]=[C:12]([C:13]([O:15]CC)=[O:14])[C:7]=2[CH:6]=[N:5]1)[CH3:3].C(O)C.[OH-].[Na+]>C1COCC1>[CH3:3][CH:2]([N:4]1[C:8]2[N:9]=[C:10]([C:18]3[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=3)[CH:11]=[C:12]([C:13]([OH:15])=[O:14])[C:7]=2[CH:6]=[N:5]1)[CH3:1]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 67124614Ethyl 1-(1-methylethyl)-6-[4-(methyloxy)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 671245231-(1-Methylethyl)-6-[4-(methyloxy)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared in the same manner as described for intermediate 58 using ethyl 1-(1-methylethyl)-6-[4-(methyloxy)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (200 mg, 0.589 mmol), Ethanol (4 mL) and THF (1 mL), and sodium hydroxide (0.982 mL, 2.95 mmol). The final product was collected as 181 mg (98%). LCMS E-S (M+H)=312.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.51-1.63 (m, 6 H), 3.85 (s, 3 H), 5.35 (m, 1 H), 7.11 (d, J=9.1 Hz, 2 H), 8.15 (s, 1 H), 8.18-8.25 (m, 2 H), 8.33 (s, 1 H), 13.95 (br. s., 1 H).

Workup

  1. customThe final product was collected as 181 mg (98%)

Sources & evidence

ORD record
ord-dd55e0ee9b374657a7cefef1a88dd428
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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