Diisobutylaluminumhydride → 1-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-(hydroxymethyl)pyridin-2(1H)-one

HRID 2203069Notes

Reaction equation

HRID 2203069 reaction equation
[CH:1]1([C:4]2[N:8]([CH3:9])[C:7]3[CH:10]=[C:11]([N:14]4[CH:19]=[CH:18][C:17]([C:20](OC)=[O:21])=[CH:16][C:15]4=[O:24])[CH:12]=[CH:13][C:6]=3[N:5]=2)[CH2:3][CH2:2]1.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[CH:1]1([C:4]2[N:8]([CH3:9])[C:7]3[CH:10]=[C:11]([N:14]4[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][C:15]4=[O:24])[CH:12]=[CH:13][C:6]=3[N:5]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 89691256HCID 89691256, compound

Product 1

HCID 896911261-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-(hydroxymethyl)pyridin-2(1H)-oneYield 47.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-2-oxo-1,2-dihydropyridine-4-carboxylate (800 mg) in DCM (20 ml) was added diisobutylaluminum hydride (1.0 M in toluene, 1.04 ml) at −78° C., and the mixture was stirred at same temperature for 2 h. The reaction mixture was then quenched with a mixture of MeOH (2 ml) and water (2 ml), filtered through celite and the resulting filtrate was concentrated in vacuo. The residue was purified by column chromatography (MeOH/DCM) to give the title compound (350 mg) as a yellow solid.

Workup

  1. customThe reaction mixture was then quenched with a mixture of MeOH (2 ml) and water (2 ml)
  2. filtrationfiltered through celite
  3. concentrationthe resulting filtrate was concentrated in vacuo
  4. customThe residue was purified by column chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-e2cda89f803e44bc837628e6344809a4
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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