Sodium Hydroxide → 1-tert-butyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 476057Notes

Reaction equation

HRID 476057 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:18]([O:20]CC)=[O:19])[C:7]3[C:12]([CH3:13])=[N:11][N:10]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:8]=3[N:9]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([C:4]2[CH:5]=[C:6]([C:18]([OH:20])=[O:19])[C:7]3[C:12]([CH3:13])=[N:11][N:10]([C:14]([CH3:17])([CH3:15])[CH3:16])[C:8]=3[N:9]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68078897ethyl 6-cyclopropyl-1-(1,1-dimethylethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 398706041-tert-butyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared in the same manner as described for intermediate 46 using ethyl 6-cyclopropyl-1-(1,1-dimethylethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (240 mg, 0.796 mmol), sodium hydroxide (4 mL, 4.00 mmol), and ethanol (30 mL), wherein the stir time was 1 h. The final product was collected as 0.210 g (96%). LCMS E-S (M+H)=274.4. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.05 (m, 4H) 1.70 (s, 9H) 2.33 (m, 1H) 2.51 (s, 3H) 7.46 (s, 1H) 13.70 (br. s., 1H).

Workup

  1. customThe final product was collected as 0.210 g (96%)

Sources & evidence

ORD record
ord-5ac7e464eb604964aee1ede9cbf002fb
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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