HCID 11676041, compound → HCID 69184168, compound

HRID 2373217Notes

Reaction equation

HRID 2373217 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)=[C:10]([C:19](OCC)=[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>C(Cl)Cl.C1(C)C=CC=CC=1>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([C:24]3[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=3)=[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

5

Reactant 2

HCID 11676041HCID 11676041, compoundHCID 21225700Diisobutylaluminumhydride2×

Product 1

HCID 69184168HCID 69184168, compoundYield 26.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of ethyl 1-ethyl-6-(4-methoxyphenyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (88 mg) in DCM (3 ml) was added 1N diisobutylaluminum hydride in toluene (0.63 ml) at −78° C. and the reaction mixtrue was stirred at −78° C. for 1.5 hours. Another 1N diisobutylaluminum hydride in toluene (0.31 ml) was added at −78° C. and the reaction mxitrue was stirred at −78° C. for 2.5 hours. The reaction mixture was quenched with brine, filtrated through celite pad, and the filtrate was concentrated in vacuo. The residue-was purified by preparative thin layer chromatography eluting with a mixture of CHCl3 and MeOH (9:1) to give [1-ethyl-6-(4-methoxyphenyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]methanol (21 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 mixture was quenched with brine
  5. filtrationfiltrated through celite pad
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue-was purified by preparative thin layer chromatography
  8. washeluting with a mixture of CHCl3 and MeOH (9:1)

Sources & evidence

ORD record
ord-07269ad574f34d57bb7faeb6b3b5b8df
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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