Lithium Hydroxide → HCID 68276009, compound

HRID 1475952Notes

Reaction equation

HRID 1475952 reaction equation
[Br:1][C:2]1[C:23]([C:24]([O:26]C)=[O:25])=[C:5]2[CH:6]=[C:7]([C:10](=[O:22])[N:11]([CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH:8]=[CH:9][N:4]2[N:3]=1.[Li+].[OH-]>C1COCC1.CO>[Br:1][C:2]1[C:23]([C:24]([OH:26])=[O:25])=[C:5]2[CH:6]=[C:7]([C:10](=[O:22])[N:11]([CH2:12][CH2:13][CH:14]([CH3:15])[CH3:16])[CH2:17][CH2:18][CH:19]([CH3:20])[CH3:21])[CH:8]=[CH:9][N:4]2[N:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68276311HCID 68276311, compound

Product 1

HCID 68276009HCID 68276009, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

To a stirred solution of methyl 2-bromo-5-(diisopentylcarbamoyl)pyrazolo[1,5-a]pyridine-3-carboxylate (0.47 g, 1.072 mmol) in THF (15 ml) and MeOH (15 ml) was added 2M aqueous LiOH solution (10.00 ml, 20 mmol). The mixture was stirred at 30° C. for 4 h then concentrated partially, acidified with 1N HCl and extracted with ethyl acetate (3×40 ml). The combined organics were dried over anhydrous sodium sulphate, filtered and concentrated. The orange solid was triturated with methyl tert-butyl ether (10 ml) to afford 2-bromo-5-(diisopentylcarbamoyl)pyrazolo[1,5-a]pyridine-3-carboxylic acid (0.291 g, 0.679 mmol, 63.3% yield) LCMS m/z 424.1, 426.1 (M+H)+, ret. time=2.21 min.

Workup

  1. concentrationthen concentrated partially
  2. extractionextracted with ethyl acetate (3×40 ml)
  3. dry with materialThe combined organics were dried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe orange solid was triturated with methyl tert-butyl ether (10 ml)

Sources & evidence

ORD record
ord-21b6f7a270ed4208985e6ddc83b9b609
Source dataset
uspto-grants-2015_04
Patent number
US09018395B2

Reaction notes

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