Cerium(III) chloride → HCID 10319338, compound

HRID 2106007Notes

Reaction equation

HRID 2106007 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].[F:5][C:6]1[CH:7]=[CH:8][C:9]([O:30][CH3:31])=[C:10]([C:12]([CH3:29])([CH3:28])[CH2:13][C:14](=[O:27])[CH2:15][N:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19](=[O:26])[CH:18]=[CH:17]2)[CH:11]=1.[CH:32]1([Mg]Br)[CH2:34][CH2:33]1>C1COCC1>[CH:32]1([C:14]([OH:27])([CH2:13][C:12]([C:10]2[CH:11]=[C:6]([F:5])[CH:7]=[CH:8][C:9]=2[O:30][CH3:31])([CH3:29])[CH3:28])[CH2:15][N:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19](=[O:26])[CH:18]=[CH:17]2)[CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 24636Cerium(III) chlorideHCID 57809771HCID 57809771, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 10319338HCID 10319338, compoundYield 1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An oven-dried round-bottomed flask charged with cerium chloride (0.27 g, 1.08 mmol) was dried under vacuum and at 140° C. for 1 hour followed by vacuum at room temperature for an additional 14 hours. The flask was sealed with a septum, evacuated under vacuum, and charged with argon. THF (3 mL) was added and the slurry was sonicated for 1 hour to give a yellow suspension. To this slurry was added 1-[4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-oxopentyl]-1H-quinolin-4-one (0.20 g, 0.54 mmol) dissolved in 1 mL of THF resulting in the formation of a dark brown solution. This was stirred for 1 hour at room temperature followed by the addition of the cyclopropylmagnesium bromide (2.18 mL, 0.5 mol/L) at 0° C. The reaction was allowed to stir at this temperature for 3 hours followed by quenching through the addition of saturated ammonium chloride (10.0 mL) resulting in the formation of a white precipitate. The biphasic system was filtered and the aqueous layer was separated. The organic layer was washed with one 25 mL portion of brine, dried over anhydrous sodium sulfite, filtered, and the solvent was evaporated in vacuo to give a yellow oil. The pure product, 1-[2-cyclopropyl-4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methylpentyl]-1H-quinolin-4-one (2.0 mg, 1%) was obtained by flash chromatography on silica gel using mixtures of EtOAc-hexanes as the eluent.

Workup

  1. customwas dried under vacuum and at 140° C. for 1 hour
  2. customThe flask was sealed with a septum
  3. customevacuated under vacuum
  4. additioncharged with argon
  5. additionTHF (3 mL) was added
  6. customthe slurry was sonicated for 1 hour
  7. customto give a yellow suspension
  8. stirringto stir at this temperature for 3 hours
  9. customby quenching through the addition of saturated ammonium chloride (10.0 mL)
  10. customresulting in the formation of a white precipitate
  11. filtrationThe biphasic system was filtered
  12. customthe aqueous layer was separated
  13. washThe organic layer was washed with one 25 mL portion of brine
  14. dry with materialdried over anhydrous sodium sulfite
  15. filtrationfiltered
  16. customthe solvent was evaporated in vacuo
  17. customto give a yellow oil

Sources & evidence

ORD record
ord-6e8705836d86494c86f9df560fe4db37
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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