Dimethylformamide → Methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(prop-1-yn-1-yl)benzoate

HRID 2177811Notes

Reaction equation

HRID 2177811 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15](OS(C(F)(F)F)(=O)=O)[C:14](C3C=COC=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:34]#[C:35][CH3:36].C(N[CH:41]([CH3:43])[CH3:42])(C)C.CN([CH:47]=[O:48])C>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([C:34]#[C:35][CH3:36])[C:14]([C:42]3[CH:41]=[CH:43][O:48][CH:47]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6335PropyneHCID 7912DiisopropylamineHCID 86677115Methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(trifluoromethanesulphonyloxy)benzoate2×

Product 1

HCID 67107923Methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(prop-1-yn-1-yl)benzoate

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

Methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(trifluoromethanesulphonyl-oxy)benzoate (Intermediate 123, 0.2 g), propyne (0.174 g), copper (I) iodide (0.008 g) and bis-(triphenylphosphine)palladium(II) chloride (0.029 g) were added to a solution of diisopropylamine (0.168 g) in DMF (2 ml) in a microwave vial. The mixture was degassed with argon and then heated in the microwave at 100° C. for 1 hour. After cooling, saturated aqueous ammonium chloride solution and ethyl acetate were added. The organic layer was separated, washed with water, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 7-25%. The resultant yellow gum was triturated with diethyl ether and the solid was collected by filtration to give methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(prop-1-yn-1-yl)benzoate (0.057 g) as a white solid.

Workup

  1. customThe mixture was degassed with argon
  2. temperatureAfter cooling
  3. additionsaturated aqueous ammonium chloride solution and ethyl acetate were added
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness
  9. customthe residue was purified by chromatography on silica
  10. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 7-25%
  11. customThe resultant yellow gum was triturated with diethyl ether
  12. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-24187ef4c68d4da79b93c89ad21a04e1
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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