Ethyl Acetate → HCID 67107342, compound

HRID 1026616Notes

Reaction equation

HRID 1026616 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7](Br)=[CH:8][CH:9]=1)=[O:4].[NH:11]1[C:19]2[C:14](=[CH:15][C:16](B(O)O)=[CH:17][CH:18]=2)[CH:13]=[CH:12]1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>O1CCOCC1.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>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:16]2[CH:15]=[C:14]3[C:19](=[CH:18][CH:17]=2)[NH:11][CH:12]=[CH:13]3)=[CH:8][CH:9]=1)=[O:4]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 605713Methyl 5-bromothiophene-2-carboxylateHCID 27343615-Indolylboronic acid

Product 1

HCID 67107342HCID 67107342, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

5-Bromothiophene-2-carboxylic acid methyl ester (0.5 g, 2.26 mmol), 1H-indol-5-ylboronic acid (0.36 g, 2.26 mmol), tetrakis(triphenylphosphine)palladium(0) (0.13 g, 0.11 mmol) and sodium carbonate (0.48 g, 4.52 mmol) were dissolved in dioxane (30 mL) and refluxed for 5 h. Ethyl acetate (30 mL) was added, and the mixture was washed with sodium bicarbonate solution. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered and purified by column chromatography to give the title compound (0.36 g, 62% Yield).

Workup

  1. temperaturerefluxed for 5 h
  2. washthe mixture was washed with sodium bicarbonate solution
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-e1b72ddd1f524bad9cead6f7ae46059c
Source dataset
uspto-grants-2014_05
Patent number
US08729273B2

Reaction notes

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