Diisobutylaluminumhydride → HCID 89690337, compound

HRID 2202990Notes

Reaction equation

HRID 2202990 reaction equation
[CH:1]1([C:4]2[N:5]=[C:6]3[CH:11]=[CH:10][C:9]([N:12]4[CH:17]=[CH:16][C:15]([C:18](OC)=[O:19])=[CH:14][C:13]4=[O:22])=[CH:8][N:7]3[C:23]=2[CH3:24])[CH2:3][CH2:2]1.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[CH:1]1([C:4]2[N:5]=[C:6]3[CH:11]=[CH:10][C:9]([N:12]4[CH:17]=[CH:16][C:15]([CH2:18][OH:19])=[CH:14][C:13]4=[O:22])=[CH:8][N:7]3[C:23]=2[CH3:24])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 121386239HCID 121386239, compound

Product 1

HCID 89690337HCID 89690337, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-2-oxo-1,2-dihydropyridine-4-carboxylate (600 mg) in DCM (10 ml) was added diisobutylaluminum hydride (1.76 M in toluene, 2.1 ml) at 78° C. The mixture was stirred at same temperature for 3 h, and allowed to warm to room temperature for 4 h. The mixture was quenched with a mixture of MeOH and water, and filtered through celite. The filtrate was concentrated in vacuo and purified by column chromatography (MeOH/DCM) to afford the title compound (200 mg) as a brown solid.

Workup

  1. customThe mixture was quenched with a mixture of MeOH and water
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. custompurified by column chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-1bb3be78c8724526a6c823fc6b8aa140
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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