Diisobutylaluminum hydride → {3-[2-Morpholin-4-yl-6-(3-pyridylamino)-4-pyridyl]phenyl}methan-1-ol

HRID 30449Notes

Reaction equation

HRID 30449 reaction equation
[N:1]1([C:7]2[CH:12]=[C:11]([C:13]3[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=3)[CH:16]=[O:17])[CH:10]=[C:9]([NH:21][C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CC(C[AlH]CC(C)C)C>C1COCC1>[N:1]1([C:7]2[CH:12]=[C:11]([C:13]3[CH:14]=[C:15]([CH2:16][OH:17])[CH:18]=[CH:19][CH:20]=3)[CH:10]=[C:9]([NH:21][C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[N:8]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 865942333-[2-Morpholin-4-yl-6-(3-pyridylamino)-4-pyridyl]benzaldehyde

Product 1

HCID 67174201{3-[2-Morpholin-4-yl-6-(3-pyridylamino)-4-pyridyl]phenyl}methan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aldehyde 39 is suspended in THF and DIBALH (1.6 N solution in THF, 3 eq) is added dropwise via a syringe. The reaction mixture is stirred at room temperature overnight, then quenched with water. The aqueous phase is extracted repeatedly with EtOAc. The organic extracts are collected and dried (Na2SO4). Evaporation of the solvent under reduced pressure and purification by reverse phase preparatory HPLC, affords compound 40.

Workup

  1. customquenched with water
  2. extractionThe aqueous phase is extracted repeatedly with EtOAc
  3. customThe organic extracts are collected
  4. dry with materialdried (Na2SO4)
  5. customEvaporation of the solvent
  6. customunder reduced pressure and purification by reverse phase preparatory HPLC

Sources & evidence

ORD record
ord-cf0fdb67d1b647268811e7b544ac6ddb
Source dataset
uspto-grants-2008_09
Patent number
US07423148B2

Reaction notes

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