Dibah → HCID 22350134, compound

HRID 896672Notes

Reaction equation

HRID 896672 reaction equation
C[O:2][C:3](=O)[CH:4]([C:29]1[CH:34]=[CH:33][C:32]([S:35][CH3:36])=[CH:31][CH:30]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:13]=[C:14]([C:22]([S:25]([CH3:28])(=[O:27])=[O:26])([CH3:24])[CH3:23])[CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)[CH:7]=1.CC(C[Al]CC(C)C)C>C(Cl)Cl>[CH3:28][S:25]([C:22]([C:14]1[CH:15]=[C:16]2[C:21](=[C:12]([C:8]3[CH:7]=[C:6]([CH2:5][CH:4]([C:29]4[CH:34]=[CH:33][C:32]([S:35][CH3:36])=[CH:31][CH:30]=4)[CH:3]=[O:2])[CH:11]=[CH:10][CH:9]=3)[CH:13]=1)[N:20]=[CH:19][CH:18]=[CH:17]2)([CH3:24])[CH3:23])(=[O:26])=[O:27]

Participants

4

Reactant 2

HCID 16682954DibahHCID 69693298HCID 69693298, compound

Product 1

HCID 22350134HCID 22350134, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 3-{3-[6-(1-methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-phenyl}-2-(4-methylsulfanyl-phenyl)-propionic acid methyl ester from Step 1 (1.48 g, 7.5 mmol) in CH2Cl2 (80 mL) at −78° C. was added dibal-H (1.6 mL, 7.8 mmol). The resulting reaction mixture was stirred 1 h at −78° C., then quenched with sodium potassium tartrate solution and stirred at 21° C. for 3 h. The organic extracts were washed (H2O), (brine), dried (MgSO4), filtered and concentrated to provided the 3-{3-[6-(1-methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-phenyl}-2-(4-methylsulfanyl-phenyl)-propionaldehyde compound as a white foam.

Workup

  1. customThe resulting reaction mixture
  2. customquenched with sodium potassium tartrate solution
  3. stirringstirred at 21° C. for 3 h
  4. washThe organic extracts were washed (H2O), (brine),
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b0c380d0ae5645669fa6eaf7e611db72
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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