Methyl Acrylate → HCID 67435854, compound

HRID 1663241Notes

Reaction equation

HRID 1663241 reaction equation
C([O-])(=O)C.[Na+].[Cl:6][C:7]1[CH:8]=[C:9]([S:14]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)(=[O:16])=[O:15])[CH:10]=[CH:11][C:12]=1[Cl:13].[C:31]([O:35][CH3:36])(=[O:34])[CH:32]=[CH2:33]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CN(C)C=O>[CH3:36][O:35][C:31](=[O:34])[CH2:32][CH:33]1[C:25]2[C:24](=[CH:29][CH:28]=[C:27]([F:30])[CH:26]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]1[S:14]([C:9]1[CH:10]=[CH:11][C:12]([Cl:13])=[C:7]([Cl:6])[CH:8]=1)(=[O:15])=[O:16]

Participants

7

Reactant 3

HCID 7294Methyl AcrylateHCID 517045Sodium AcetateHCID 67437892HCID 67437892, compound

Product 1

HCID 67435854HCID 67435854, compoundYield 44.2%

Reagents, catalysts & solvents 3

HCID 165397Cupric acetate monohydrateCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Sodium acetate (370 mg, 4.5 mmol) was dried in a 100 mL two-necked flask at 150° C. in vacuo for 2 hours, then palladium acetate (100.8 mg 0.45 mmol), copper(II) acetate hydrate (90.0 mg, 0.45 mmol), 3,4-dichloro-N-(4′-fluoro-biphenyl-2-yl)-benzenesulfonamide (3.58 g, 9 mmol), methyl acrylate (2.32 g, 27 mmol), 4 Å molecular sieves (3.6 g) and dimethyl formamide (45 mL) were added, and the resulting mixture was stirred at 120° C. for 16 hours. After cooling the reaction mixture was concentrated, then diluted with water (50 mL) and extracted with diethyl ether (2×30 mL), dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography using Kieselgel 60 (0.015-0.040 mm) as adsorbent (Merck) and n-hexane:ethyl-acetate=4:1 as eluent to yield 1.91 g (44%) of the title compound as white crystals.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. concentrationwas concentrated
  3. additiondiluted with water (50 mL)
  4. extractionextracted with diethyl ether (2×30 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-634395daf8774a5685e2370762138d3f
Source dataset
uspto-grants-2011_10
Patent number
US08034827B2

Reaction notes

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