Ammonium Chloride → (5R)-5-[(E)-2-(5-benzyl-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one

HRID 70676Notes

Reaction equation

HRID 70676 reaction equation
[Br-].[CH2:2]([Zn+])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.Br[C:27]1[CH:28]=[CH:29][C:30](/[C:35](/[C:43]2[CH:48]=[CH:47][C:46]([C:49]([CH3:52])([CH3:51])[CH3:50])=[CH:45][CH:44]=2)=[CH:36]/[C@@H:37]2[NH:41][C:40](=[O:42])[CH2:39][CH2:38]2)=[N:31][C:32]=1[O:33][CH3:34].[Cl-].[NH4+]>O1CCCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:2]([C:27]1[CH:28]=[CH:29][C:30](/[C:35](/[C:43]2[CH:44]=[CH:45][C:46]([C:49]([CH3:52])([CH3:51])[CH3:50])=[CH:47][CH:48]=2)=[CH:36]/[C@@H:37]2[NH:41][C:40](=[O:42])[CH2:39][CH2:38]2)=[N:31][C:32]=1[O:33][CH3:34])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 521585Tris(furan-2-yl)phosphaneHCID 58452636(5R)-5-[(E)-2-(5-bromo-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-oneHCID 178419772HCID 178419772, compound

Product 1

HCID 67397174(5R)-5-[(E)-2-(5-benzyl-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

0.05 M benzylzinc(II) bromide (385 μL), tris(dibenzylideneacetone)dipalladium(0) (8.0 mg) and tri(2-furyl)phosphine (15 mg) were added to a solution of (5R)-5-[(E)-2-(5-bromo-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one obtained in Reference Example 4-42(2) (30 mg) in tetrahydrofuran (2 mL), and the mixture was stirred under microwave irradiation at 110° C. for one hour. An ammonium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→1:0) to give (5R)-5-[(E)-2-(5-benzyl-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one (23 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→1:0)

Sources & evidence

ORD record
ord-bfbfcc32e518474d9d9767bb8c3d6ad7
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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