Sodium Hydroxide → HCID 58316724, compound

HRID 1426239Notes

Reaction equation

HRID 1426239 reaction equation
COC([C:5]1[C:6]([C:15]([CH3:18])([CH3:17])[CH3:16])=[N:7][N:8]2[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][C:9]=12)=O.[OH-].[Na+]>OS(O)(=O)=O.O>[Br:14][C:12]1[CH:11]=[CH:10][C:9]2[N:8]([N:7]=[C:6]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:5]=2)[CH:13]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58316720HCID 58316720, compound

Product 1

HCID 58316724HCID 58316724, compoundYield 41.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 6-bromo-2-tert-butyl-pyrazolo[1,5-a]pyridine-3-carboxylic acid methyl ester (example 41, step 2) (1.1 g, 3.53 mmol) in H2SO4 (5 ml) and H2O (5 ml) was heated at 80° C. for 36 hours. The reaction mixture was neutralized with 2N sodium hydroxide and extracted with ethyl acetate (4×60 ml). The organic extracts were dried with sodium sulfate, filtered and evaporated to dryness. The crude product was purified by flash chromatography on silica gel (heptane:EtOAc 95:5→90:10). The desired 6-bromo-2-tert-butyl-pyrazolo[1,5-a]pyridine (370 mg, 38% yield) was obtained as a white solid, MS: m/e=254.2 (M+H+).

Workup

  1. extractionextracted with ethyl acetate (4×60 ml)
  2. dry with materialThe organic extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude product was purified by flash chromatography on silica gel (heptane:EtOAc 95:5→90:10)

Sources & evidence

ORD record
ord-9665b3bb0a9b4fb1908fad245dc4324c
Source dataset
uspto-grants-2015_01
Patent number
US08933094B2

Reaction notes

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