Water → HCID 86761015, compound

HRID 1437684Notes

Reaction equation

HRID 1437684 reaction equation
Cl.[F:2][C:3]([F:31])([F:30])[C:4]1[CH:5]=[C:6]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][NH:12][CH2:11][C@H:10]1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1.Br[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.CC(C)([O-])C.[Na+].O>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]>[F:31][C:3]([F:30])([F:2])[C:4]1[CH:5]=[C:6]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][N:12]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:11][C@H:10]1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7961BromobenzeneHCID 23676156Sodium t-butoxideHCID 86761016HCID 86761016, compound

Product 1

HCID 86761015HCID 86761015, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of the compound (200 mg) obtained in Example 509, bromobenzene (0.054 ml), tris(dibenzylideneacetone)dipalladium(0) (11 mg) and sodium tert-butoxide (94 mg) in toluene (5.0 ml), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl((±)-BINAP) (7.3 mg) was added, and the reaction mixture was stirred at 85° C. for 17 hours under argon atmosphere. The reaction mixture was poured into water, and then the product was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried, and then the solvent was evaporated under reduced pressure. The obtained residue was isolated and purified by silica gel column chromatography (ethyl acetate hexane=1:10→1:4) to obtain the title compound as colorless oil (120 mg, 55%).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was isolated
  6. custompurified by silica gel column chromatography (ethyl acetate hexane=1:10→1:4)

Sources & evidence

ORD record
ord-162da35abeab40e2ade419bdd6239758
Source dataset
uspto-grants-2009_11
Patent number
US07622487B2

Reaction notes

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