Propyne → HCID 86748034, compound

HRID 1741623Notes

Reaction equation

HRID 1741623 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:6][CH:7]=1.[CH:18]#[C:19][CH3:20]>CS(C)=O.C(N(CC)CC)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:18]([C:2]1[CH:3]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:6][CH:7]=1)#[C:19][CH3:20]

Participants

6

Reactant 2

HCID 6335PropyneHCID 14097639HCID 14097639, compound

Product 1

HCID 86748034HCID 86748034, compound

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 679Dimethyl SulfoxideSolventHCID 8471TriethylamineSolvent

Procedure

A stirred mixture of 3 g of 5-bromo-pyridine-2,3-dicarboxylic acid, diethyl ester, 0.1 g cuprous iodide and 0.7 g bis(triphenylphosphine)palladium(II)chloride in 40 mL dimethyl sulfoxide and 12 mL triethylamine is cooled to 10°, and 10 mL of liquid propyne is added. The reaction is stirred at room temperature thereafter for 16 hours, then is poured onto water and extracted with methylene chloride. The organic phase is washed with dilute hydrochloric acid, then water, then brine, and dried. Concentration in vacuo, and chromatography of the residue on silica gel using ether-hexane mixture affords the desired product as an oil.

Workup

  1. temperatureis cooled to 10°
  2. additionis poured onto water
  3. extractionextracted with methylene chloride
  4. washThe organic phase is washed with dilute hydrochloric acid
  5. dry with materialwater, then brine, and dried
  6. concentrationConcentration in vacuo, and chromatography of the residue on silica gel

Sources & evidence

ORD record
ord-215a76d3645f4ffb9e12de01fe7d473c
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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