Cesium carbonate → HCID 67400008, compound

HRID 70700Notes

Reaction equation

HRID 70700 reaction equation
Br/[CH:2]=[C:3](/[C:14]1[N:19]=[C:18]([O:20][CH3:21])[C:17]([Cl:22])=[CH:16][CH:15]=1)\[C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:6][CH:5]=1.[NH:23]1[CH2:27][CH2:26][CH2:25][C:24]1=[O:28].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[C:10]([C:7]1[CH:8]=[CH:9][C:4](/[C:3](/[C:14]2[CH:15]=[CH:16][C:17]([Cl:22])=[C:18]([O:20][CH3:21])[N:19]=2)=[CH:2]\[N:23]2[CH2:27][CH2:26][CH2:25][C:24]2=[O:28])=[CH:5][CH:6]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 634876Binap, (A+-)-HCID 58452310HCID 58452310, compound

Product 1

HCID 67400008HCID 67400008, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

A solution of 6-[(E)-2-bromo-1-(4-tert-butylphenyl)ethenyl]-3-chloro-2-methoxypyridine obtained in Reference Example 4-7 (109 mg), 2-pyrrolidone (73 mg), tris(dibenzylideneacetone)dipalladium(0) (11 mg), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (22 mg) and cesium carbonate (329 mg) in toluene (3 mL) was stirred at an external temperature of 130° C. for four hours in a nitrogen atmosphere. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→1:1) to give 1-[(E)-2-(4-tert-butylphenyl)-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one as a yellow powder (82 mg, 75%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→1:1)

Sources & evidence

ORD record
ord-b51199273cbc416eb7e2ad12e5be6267
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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