Sodium Carbonate → Ethyl 2-(5-methyl-2-benzofuranyl)benzoate

HRID 1492761Notes

Reaction equation

HRID 1492761 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[C:12]2[CH:13]=[C:14]([CH2:17]N3C(C(NCC)=O)=C(Cl)N=C3CCCC)[CH:15]=[CH:16][C:11]=2[O:10][C:9]=1C1C=CC=CC=1C1N=NN(C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)N=1.Br[C:64]1[CH:74]=[CH:73][CH:72]=[CH:71][C:65]=1[C:66]([O:68][CH2:69][CH3:70])=[O:67]>COCCOC.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.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:17][C:14]1[CH:15]=[CH:16][C:11]2[O:10][C:9]([C:64]3[CH:74]=[CH:73][CH:72]=[CH:71][C:65]=3[C:66]([O:68][CH2:69][CH3:70])=[O:67])=[CH:8][C:12]=2[CH:13]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 80186Ethyl 2-bromobenzoateHCID 545415391-[[3-Bromo-2-[2-[2-(triphenylmethyl)-2H-tetrazol-5-yl]phenyl]-5-benzofuranyl]methyl]-2-butyl-4-chloro-N-ethyl-1H-imidazole-5-carboxamide

Product 1

HCID 18950932Ethyl 2-(5-methyl-2-benzofuranyl)benzoateYield 313.2%

Reagents, catalysts & solvents 2

HCID 178527695HCID 178527695, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Sodium carbonate (1N; 60 ml) was added to a mixture of Intermediate 1 (4.7 g), ethyl 2-bromobenzoate (5.89 g) and tetrakis- triphenylphosphine palladium (0) (0.88 g) in DME (100 ml). The mixture was heated at reflux for 18 h, cooled to room temperature and then concentrated in vacuo. The residue was extracted with ether (3×100 ml) and the combined extracts washed with brine (1×100 ml) and dried. The solvent was evaporated to give a brown oil (5 g) which was purified by column chromatography eluting with System A (1:20) to give the title compound as a pale yellow oil (2.89 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 h
  3. concentrationconcentrated in vacuo
  4. extractionThe residue was extracted with ether (3×100 ml)
  5. washthe combined extracts washed with brine (1×100 ml)
  6. customdried
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-6a7887bcdc524a1d885e3ecd3d223d0c
Source dataset
uspto-grants-1994_12
Patent number
US05374646

Reaction notes

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