Methanol → HCID 117798896, compound

HRID 1497387Notes

Reaction equation

HRID 1497387 reaction equation
[CH3:1][N:2]1[C:10]([CH3:11])=[C:9]2[C:4]([CH:5]=[CH:6][C:7]([N:12]3[CH:17]=[CH:16][C:15]([C:18](OC)=[O:19])=[CH:14][C:13]3=[O:22])=[CH:8]2)=[N:3]1.[H-].C([Al+]CC(C)C)C(C)C.CO.O>ClCCl>[CH3:1][N:2]1[C:10]([CH3:11])=[C:9]2[C:4]([CH:5]=[CH:6][C:7]([N:12]3[CH:17]=[CH:16][C:15]([CH2:18][OH:19])=[CH:14][C:13]3=[O:22])=[CH:8]2)=[N:3]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 118534016HCID 118534016, compound

Product 1

HCID 117798896HCID 117798896, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 1-(2,3-dimethyl-2H-indazol-5-yl)-2-oxo-1,2-dihydropyridine-4-carboxylate (450 mg) in dichloromethane (40 ml) was added diisobutylaluminum hydride (1 M toluene solution, 7.5 ml) at −78° C., and the mixture was stirred at the same temperature for 2 hr. To the reaction mixture were added methanol and water at the same temperature, and the mixture was filtered through celite, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (dichloromethane/methanol) to give the title compound (220 mg).

Workup

  1. filtrationthe mixture was filtered through celite
  2. concentrationconcentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-7ecea291edeb40bb8c632ad91ba6477f
Source dataset
uspto-grants-2015_12
Patent number
US09199963B2

Reaction notes

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