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Water → (5R)-5-{(E)-2-(5-chloro-6-methoxypyridin-2-yl)-2-[4-(propan-2-yl)phenyl]ethenyl}-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

HRID 70637
Notes
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Reaction equation

HRID 70637 reaction equation
Br[C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([Cl:10])=[CH:4][CH:3]=1.[F-].[Cs+].[CH3:13][O:14][C:15]1[CH:51]=[C:50]([O:52][CH3:53])[CH:49]=[CH:48][C:16]=1[CH2:17][N:18]1[C@@H:22](/[CH:23]=[C:24](\[C:38]2[CH:43]=[CH:42][C:41]([CH:44]([CH3:46])[CH3:45])=[CH:40][CH:39]=2)/[Sn](CCCC)(CCCC)CCCC)[CH2:21][CH2:20][C:19]1=[O:47].O>CN(C)C=O.[Cu](I)I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[Cl:10][C:5]1[CH:4]=[CH:3][C:2](/[C:24](/[C:38]2[CH:39]=[CH:40][C:41]([CH:44]([CH3:46])[CH3:45])=[CH:42][CH:43]=2)=[CH:23]/[C@@H:22]2[N:18]([CH2:17][C:16]3[CH:48]=[CH:49][C:50]([O:52][CH3:53])=[CH:51][C:15]=3[O:14][CH3:13])[C:19](=[O:47])[CH2:20][CH2:21]2)=[N:7][C:6]=1[O:8][CH3:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 962WaterHCID 25953Cesium fluorideHCID 58452258(5R)-1-(2,4-dimethoxybenzyl)-5-[(E)-2-[4-(propan-2-yl)phenyl]-2-(tributylstannyl)ethenyl]pyrrolidin-2-oneHCID 584523026-Bromo-3-chloro-2-methoxypyridine

Product 1

HCID 67397494(5R)-5-{(E)-2-(5-chloro-6-methoxypyridin-2-yl)-2-[4-(propan-2-yl)phenyl]ethenyl}-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

6-bromo-3-chloro-2-methoxypyridine (361 mg), cesium fluoride (246 mg), copper iodide (170 mg) and tetrakis(triphenylphosphine)palladium(0) (92 mg) were added to a solution of (5R)-1-(2,4-dimethoxybenzyl)-5-[(E)-2-[4-(propan-2-yl)phenyl]-2-(tributylstannyl)ethenyl]pyrrolidin-2-one obtained in Reference Example 4-27 (543 mg) in N,N-dimethylformamide (6 mL), and the mixture was stirred at 65° C. for 1.5 hours. Water and ethyl acetate were added to the reaction solution. After filtration through celite, the organic layer was washed with brine. The organic layer dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→0:1) to give (5R)-5-{(E)-2-(5-chloro-6-methoxypyridin-2-yl)-2-[4-(propan-2-yl)phenyl]ethenyl}-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one as a yellow oil (268 mg).

Workup

  1. filtrationAfter filtration through celite
  2. washthe organic layer was washed with brine
  3. dry with materialThe organic layer dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customafter which the solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→0:1)

Sources & evidence

ORD record
ord-5d0cd933178c4fa0b238c6c3fefe6439
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822503B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes