Diisobutylaluminumhydride → HCID 89690255, compound

HRID 2202993Notes

Reaction equation

HRID 2202993 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:16])=[C:9]([C:11](OCC)=[O:12])[N:10]=2)[CH:7]=1.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:16])=[C:9]([CH:11]=[O:12])[N:10]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 121386250HCID 121386250, compound

Product 1

HCID 89690255HCID 89690255, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethyl 6-iodo-3-methylimidazo[1,2-a]pyridine-2-carboxylate (2.0 g) in DCM (40 ml) was added diisobutylaluminum hydride (1.0 M solution in toluene, 8 ml) at −78° C., and the resultant mixture was stirred at same temperature for 3 h. The reaction mixture was quenched with MeOH (10 ml) and 2 M HCl (15 ml), and basified with saturated aqueous NaHCO3 solution (20 ml) at 0° C. The mixture was extracted with DCM, washed with brine, dried over Na2SO4, concentrated in vacuo and purified by column chromatography (MeOH/DCM) to afford the title compound (1.2 g) as a light yellow solid.

Workup

  1. customThe reaction mixture was quenched with MeOH (10 ml) and 2 M HCl (15 ml)
  2. custombasified with saturated aqueous NaHCO3 solution (20 ml) at 0° C
  3. extractionThe mixture was extracted with DCM
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-a3e4d49bdafd4e5ca96b9a2c1ffe4996
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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