Cesium carbonate → HCID 11552467, compound

HRID 747573Notes

Reaction equation

HRID 747573 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10](=[O:21])[NH:11][C@@H:12]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[CH3:13])=[CH:8][CH:9]=1)=[O:4].[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1B(O)O.C([O-])([O-])=O.[Cs+].[Cs+]>C(COC)OC.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10](=[O:21])[NH:11][C@@H:12]([C:14]2[CH:19]=[CH:18][C:17]([C:23]3[S:22][CH:26]=[CH:25][CH:24]=3)=[CH:16][CH:15]=2)[CH3:13])=[CH:8][CH:9]=1)=[O:4]

Participants

7

Reactant 3

HCID 10796Cesium carbonate2×HCID 27339602-Thiopheneboronic acid2×HCID 11537926HCID 11537926, compound

Product 1

HCID 11552467HCID 11552467, compoundYield 49.9%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a suspension of 0.462 g (0.0004 mol) tetrakis(triphenylphosphine)-palladium(0) in 45 ml dry dimethoxyethane, 5.00 g (0.0136 mol) (R)-5-[1-(4-bromo-phenyl)-ethylcarbamoyl]-thiophene-2-carboxylic acid methyl ester were added and stirred for 10 min at room temperature under nitrogen atmosphere. 3.65 g (0.0285 mol) thiophene-2-boronic acid in 20 ml ethanol and 14.3 ml (0.0286 mol) of a 2 M aqueous solution of Cs2CO3 were added and the mixture was heated to 75-80° C. for 3 hours. After 1.25 hours, another 0.5 equivalents of thiophene-2-boronic acid and Cs2CO3 were added to the mixture. The warm reaction mixture was filtered, the solid was washed with ethyl acetate and the solvent of the filtrates was evaporated. The residue was dissolved in dichloromethane, washed with water, dried over magnesium sulfate and the solvent was removed. The crude product was recrystallized from n-butanol/n-heptane 1:2 and dried in vacuum to give 2.52 g (0.00678 mol) (R)-5-[1-(4-thiophen-2-yl-phenyl)-ethylcarbamoyl]-thiophene-2-carboxylic acid methyl ester.

Workup

  1. additionwere added
  2. temperaturethe mixture was heated to 75-80° C. for 3 hours
  3. waitAfter 1.25 hours
  4. customThe warm reaction mixture
  5. filtrationwas filtered
  6. washthe solid was washed with ethyl acetate
  7. customthe solvent of the filtrates was evaporated
  8. dissolutionThe residue was dissolved in dichloromethane
  9. washwashed with water
  10. dry with materialdried over magnesium sulfate
  11. customthe solvent was removed
  12. customThe crude product was recrystallized from n-butanol/n-heptane 1:2
  13. customdried in vacuum

Sources & evidence

ORD record
ord-ad4c29073193481e9e071e38bfda27dc
Source dataset
uspto-grants-2008_07
Patent number
US07396944B2

Reaction notes

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