Ethanol → HCID 67005920, compound

HRID 563447Notes

Reaction equation

HRID 563447 reaction equation
Cl[C:2]1[C:7]([CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]([CH3:15])([CH3:14])[C:10]([O:12]C)=[O:11])=[CH:6][N:5]=[C:4]2[N:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:23]=[CH:24][C:3]=12.C(N(C(C)C)CC)(C)C.C(O)C.O.[OH-].[Li+]>[Pd].O1CCOCC1.O>[CH3:14][C:9]([CH3:15])([CH:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:7]1[CH:2]=[C:3]2[CH:24]=[N:23][N:22]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:4]2=[N:5][CH:6]=1)[C:10]([OH:12])=[O:11]

Participants

8

Reactant 4

HCID 702EthanolHCID 81531DiisopropylethylamineHCID 168937Lithium hydroxide, monohydrateHCID 59252843HCID 59252843, compound

Product 1

HCID 67005920HCID 67005920, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 3-(4-chloro-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-2,2-dimethyl-3-phenylpropanoate (27 mg, 0.064 mmol), palladium (10% on carbon, 10 mg), diisopropylethylamine (0.017 mL, 0.096 mmol), and ethanol (3 mL) was stirred under hydrogen balloon for 80 min. The mixture was then filtered through a pad of silica gel and concentrated. The residue was mixed with lithium hydroxide monohydrate (30 mg, 0.7 mmol), water (1 mL), and dioxane (1 mL), and stirred at 110° C. overnight. After cooled, the mixture was partitioned between water and diethyl ether. The ether layer was extracted with water. Combined aqueous solutions were acidified with 10% citric acid aqueous solution and extracted with ethyl acetate. Combined extracts were washed with brine, dried (Na2SO4) and concentrated to give 2,2-dimethyl-3-phenyl-3-(1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)propanoic acid (16 mg, 0.043 mmol, 69% yield).

Workup

  1. filtrationThe mixture was then filtered through a pad of silica gel
  2. concentrationconcentrated
  3. stirringstirred at 110° C. overnight
  4. temperatureAfter cooled
  5. customthe mixture was partitioned between water and diethyl ether
  6. extractionThe ether layer was extracted with water
  7. extractionextracted with ethyl acetate
  8. washCombined extracts were washed with brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-3b36a9e812ad4889bbc2f98719ad1bbf
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

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