Potassium Carbonate → HCID 69671050, compound

HRID 1191677Notes

Reaction equation

HRID 1191677 reaction equation
Br[C:2](Br)=[CH:3][C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH3:12])[CH:7]=[CH:6][C:5]=1[NH:13][CH2:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[C:18]([O:20][CH3:21])=[O:19].[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.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]>[CH2:11]([O:10][C:8]1[CH:9]=[C:4]2[C:5](=[CH:6][CH:7]=1)[N:13]([CH2:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[C:18]([O:20][CH3:21])=[O:19])[C:2]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[CH:3]2)[CH3:12]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 80271Tri-o-tolylphosphineHCID 86665741HCID 86665741, compound

Product 1

HCID 69671050HCID 69671050, compoundYield 65.1%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

A suspension of methyl 3-{[2-(2,2-dibromovinyl)-4-ethoxyphenylamino]methyl}benzoate (258 mg), phenylboronic acid (134 mg), tris(dibenzylideneacetone)dipalladium (0) (25.1 mg), tris(2-methylphenyl)phosphine and potassium carbonate (381 mg) in toluene (5 mL) was stirred at 85° C. for 3.5 hours under an argon atmosphere. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and filtered through celite (registered trademark). The filtrate was concentrated under reduced pressure. The residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (138 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through celite (registered trademark)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-fa7b5892ed0f4ffe96167020af1f66e2
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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