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

HRID 1522478Notes

Reaction equation

HRID 1522478 reaction equation
[CH3:1][CH:2]([N:4]1[C:8]2[N:9]=[C:10]([C:18]3[CH:23]=[CH:22][N:21]=[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][N:21]=[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 67124442Ethyl 1-(1-methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 201146251-(1-Methylethyl)-6-(4-pyridinyl)-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-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (100 mg, 0.322 mmol), ethanol (4 mL), THF (0.8 mL), and sodium hydroxide (0.537 mL, 1.611 mmol). The final product was collected as 88 mg (97%). LCMS E-S (M+H)=283.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.58 (d, J=6.4 Hz, 6 H), 5.40 (m, 1 H), 8.25 (d, J=5.6 Hz, 2 H), 8.32 (s, 1 H), 8.44 (s, 1 H), 8.79 (d, J=5.6 Hz, 2 H), 14.12 (br. s., 1 H).

Workup

  1. customThe final product was collected as 88 mg (97%)

Sources & evidence

ORD record
ord-40531336986243f187269ae36bb59ab5
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

Loading…