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