HCID 60207309, compound → HCID 46932144, compound

HRID 1192048Notes

Reaction equation

HRID 1192048 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:16](=[O:18])[CH3:17])[S:5][C:6]=1[S:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[Cl:15].[Cu][C:20]#[N:21]>N1C=CC=CC=1.S([O-])([O-])(=O)=O.[Cu+2]>[C:20]([C:2]1[CH:3]=[C:4]([C:16](=[O:18])[CH3:17])[S:5][C:6]=1[S:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[Cl:15])#[N:21]

Participants

5

Reactant 2

HCID 60207309HCID 60207309, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 46932144HCID 46932144, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 1049PyridineSolvent

Procedure

To a CEM microwave tube, was charged with 1-[4-bromo-5-(2,4-dichlorophenyl)sulfanyl-2-thienyl]ethanone as prepared in example 21 (0.6 g, 1.6 mmol), copper(I) cyanide (0.85 g, 9.4 mmol), and pyridine (5 mL) as solvent. The mixture was subjected to microwave irradiation (200 W) on a CEM Discovery™ microwave machine at 150° C. for 30 minutes. After the irradiation, the mixture was cooled to ambient temperature and treated with 20 mL of saturated copper(II) sulfate aqueous solution and extracted with ethyl acetate. The combined organic layer was separated, washed with water, dried (Na2SO4) and concentrated. The crude was purified by silica gel chromatography using a 96:4 mixture of hexane and ethyl acetate as eluent to afford the title product (0.515 g, 78% yield). 1H NMR (400 MHz, CDCl3) δ: 7.69 (1H, s), 7.56 (1H, m), 7.53 (1H, m), 7.33 (1H, m), 2.51 (3H, s). MS m/z: 326.2 [M+H]+.

Workup

  1. customThe mixture was subjected to microwave irradiation (200 W) on a CEM Discovery™ microwave machine at 150° C. for 30 minutes
  2. customAfter the irradiation
  3. extractionextracted with ethyl acetate
  4. customThe combined organic layer was separated
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude was purified by silica gel chromatography
  9. additiona 96:4 mixture of hexane and ethyl acetate as eluent

Sources & evidence

ORD record
ord-2cda6ab1389443359482e8d5269d3b27
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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