Diisobutylaluminumhydride → HCID 86691853, compound

HRID 1616237Notes

Reaction equation

HRID 1616237 reaction equation
[CH3:1][C:2]([CH3:27])([CH3:26])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=3[CH3:23])[C:16](OC)=[O:17])=[CH:10][CH:11]=2)[N:6]([CH3:24])[C:5]1=[O:25].[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[CH3:1][C:2]([CH3:27])([CH3:26])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH:14]=[C:15]([CH2:16][OH:17])[CH:20]=[CH:21][C:22]=3[CH3:23])=[CH:10][CH:11]=2)[N:6]([CH3:24])[C:5]1=[O:25]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 86691854HCID 86691854, compound

Product 1

HCID 86691853HCID 86691853, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Methyl 3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]-4-methylbenzoate (15-4) (570 mg, 1.6 mmol, 1.0 eq.) was dissolved in dry THF (6.2 mL) and cooled to −78° C. Diisobutylaluminum hydride (6.2 mL, 6.2 mmol, 4.0 eq, 1M in heptane) was carefully added under nitrogen. The resulting mixture stirred at −78° C. for 10 minutes. The reaction was warmed to 0° C. and quenched with a saturated solution of Rochelle's Salt (5 mL). The resulting mixture was warmed to ambient temperature and stirred for 2 hours. The mixture was then extracted with ethyl acetate and the combined organics were washed with water and brine, dried over magnesium sulfate, filtered and concentrated to afford 1-(2,2-dimethylpropyl)-5-[5-(hydroxymethyl)-2-methylphenyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (51-1) as a white solid. MS (M+H)+: observed=340.2021, calculated=340.2020.

Workup

  1. temperatureThe reaction was warmed to 0° C.
  2. customquenched with a saturated solution of Rochelle's Salt (5 mL)
  3. temperatureThe resulting mixture was warmed to ambient temperature
  4. stirringstirred for 2 hours
  5. extractionThe mixture was then extracted with ethyl acetate
  6. washthe combined organics were washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-7ef1fc23525d4907a1786d65d5c05b41
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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