Diisobutylaluminum hydride → HCID 18187305, compound

HRID 1357653Notes

Reaction equation

HRID 1357653 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[NH:6][C:7]3[N:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]([C:17]#N)([CH:14]([F:16])[F:15])[C:4]=2[CH:3]=1.CC(C[AlH]CC(C)C)C.CC[O:32]C(C)=O.CCCCCC>C(Cl)Cl>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[NH:6][C:7]3[N:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]([CH:14]([F:16])[F:15])([CH:17]=[O:32])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 18187277HCID 18187277, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 18187305HCID 18187305, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Method LLL To a stirred solution of 7-chloro-5-cyano-5-(difluoromethyl)-5,10-dihydrobenzo[b][1,8]naphthyridine (92) (747 mg, 2.55 mmol) in anhydrous methylene chloride (40 mL) at −78° C. was added DIBAL (1.0 M in CH2Cl2, 7.67 mL) dropwise. After 3 h at −50° C., the reaction was quenched with 1.0 N HCl (40 mL), and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Flash chromatography (SiO2, 30% EtOAc-hexane) furnished 93 (299 mg, 39% yield) as a yellow solid.

Workup

  1. customthe reaction was quenched with 1.0 N HCl (40 mL)
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-933d95a0c333409882256880212c5aba
Source dataset
uspto-grants-2003_07
Patent number
US06593337B1

Reaction notes

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