Sodium Carbonate → HCID 67146652, compound

HRID 2422218Notes

Reaction equation

HRID 2422218 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].Br[C:46]1[CH:50]=[CH:49][S:48][CH:47]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[S:48]1[CH:49]=[CH:50][C:46]([C:2]2[CH:3]=[C:4]([CH2:8][O:9][C:10]3[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=3)[CH:5]=[CH:6][CH:7]=2)=[CH:47]1

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 133833-BromothiopheneHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 23136270Methyl 4-[(3-bromophenyl)methoxy]benzenepropanoate

Product 1

HCID 67146652HCID 67146652, compoundYield 22.9%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 4-[(3-bromophenyl)methoxy]benzenepropanoate (0.96 g, 2.8 mmol), bis(pinacolato)diboron (0.77 g, 3.0 mmol) and potassium acetate (0.81 g, 8.3 mmol) were dissolved in N,N-dimethylformamide (30 mL) and, after argon substitution, 1,1′-bis(diphenyphosphino)ferrocenedichloropalladium (II) (0.067 g, 0.083 mmol) was added. The reaction mixture was heated overnight under an argon atmosphere at 80° C. The reaction mixture was cooled, and 3-bromothiophene (0.43 g, 2.6 mmol), 1,1′-bis(diphenyphosphino)ferrocenedichloropalladium (II) (0.067 g, 0.083 mmol) and 2N aqueous sodium carbonate solution (6.9 mL, 14 mmol) were added to the reaction mixture. The reaction mixture was heated overnight under an argon atmosphere at 80° C. The reaction mixture was cooled, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=15:1) to give the title compound (0.21 g, yield 22%) as an oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. temperatureThe reaction mixture was heated overnight under an argon atmosphere at 80° C
  3. temperatureThe reaction mixture was cooled
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=15:1)

Sources & evidence

ORD record
ord-639512e46527402cbba377352566ae52
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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