HCID 11710689, compound → HCID 11688198, compound

HRID 2373215Notes

Reaction equation

HRID 2373215 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:26][O:27][CH3:28])=[C:10]([C:19](OC(C)(C)C)=[O:20])[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:26][O:27][CH3:28])=[C:10]([CH2:19][OH:20])[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 11710689HCID 11710689, compoundHCID 21225700Diisobutylaluminumhydride3×

Product 1

HCID 11688198HCID 11688198, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent4×

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of tert-butyl 1-ethyl-6-(methoxymethyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (100 mg) in toluene (2.5 ml) was added 1N diisobutylaluminum hydride in toluene (0.92 ml) at −78° C. and the reaction mixtrue was stirred at −78° C. for 1.5 hour. Another 1N diisobutylaluminum hydride in toluene (0.4 ml) was added at −78° C. and the reaction mxitrue was stirred at −78° C. for 2.5 hours. Another 1N diisobutylaluminum hydride in toluene (0.52 ml) was added at −78° C. and the reaction mxitrue was stirred at −78° C. for 1 hour. The reaction mixture was quenched with brine, filtrated through celite pad, and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a mixture of EtOAc and n-hexane (2:1) to give [1-ethyl-6-(methoxymethyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]methanol (53 mg) as a light yellow oil.

Workup

  1. customthe reaction
  2. customthe reaction
  3. stirringmxitrue was stirred at −78° C. for 2.5 hours
  4. customthe reaction
  5. stirringmxitrue was stirred at −78° C. for 1 hour
  6. customThe reaction mixture was quenched with brine
  7. filtrationfiltrated through celite pad
  8. concentrationthe filtrate was concentrated in vacuo
  9. customThe residue was purified by flash column chromatography on silica gel eluting with a mixture of EtOAc and n-hexane (2:1)

Sources & evidence

ORD record
ord-1b00e7d86aa847bea014b7ac6dae2e91
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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