HCID 22350134, compound → HCID 22350120, compound

HRID 896673Notes

Reaction equation

HRID 896673 reaction equation
[CH3:1][S:2]([C:5]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([CH2:24][CH:25]([C:28]4[CH:33]=[CH:32][C:31]([S:34][CH3:35])=[CH:30][CH:29]=4)[CH:26]=[O:27])[CH:21]=[CH:22][CH:23]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([CH3:7])[CH3:6])(=[O:4])=[O:3].[C:36]1([Mg]Cl)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(Cl)Cl.[Cl-].[NH4+].C(OCC)(=O)C>[CH3:1][S:2]([C:5]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([CH2:24][CH:25]([C:28]4[CH:33]=[CH:32][C:31]([S:34][CH3:35])=[CH:30][CH:29]=4)[CH:26]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[OH:27])[CH:21]=[CH:22][CH:23]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([CH3:7])[CH3:6])(=[O:3])=[O:4]

Participants

6

Reactant 2

HCID 22350134HCID 22350134, compoundHCID 178478979HCID 178478979, compound

Product 1

HCID 22350120HCID 22350120, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
21 °C

Procedure

To a solution of 3-{3-[6-(1-methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-phenyl}-2-(4-methylsulfanyl-phenyl)-propionaldehyde from Step 2 (150 mg, 0.3 mmol) in CH2Cl2 (6 mL) at 21° C. was added phenylmagnesium chloride (2M, TBF, 0.45 mL, 0.9 mmol) dropwise. The resulting reaction mixture was stirred 0.5 h at 21° C. then diluted with a saturated ammonium chloride solution and ethyl acetate. The organic extracts were washed (H2O), (brine), dried (MgSO4), filtered and concentrated. The crude oil was used as such in the next step.

Workup

  1. customThe resulting reaction mixture
  2. washThe organic extracts were washed (H2O), (brine),
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-840b9ba81e6f4dc7a00cec577858a710
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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