Dodecane → HCID 21110086, compound

HRID 1766148Notes

Reaction equation

HRID 1766148 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]([O:12][CH3:13])=[O:11])=[CH:2]1.I[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C@@H]1(N)CCCC[C@H]1N.CCCCCCCCCCCC>[Cu]I.O.C(OCC)(=O)C.O1CCOCC1>[N:18]1[CH:19]=[CH:20][C:15]([N:1]2[C:5]3=[N:6][CH:7]=[CH:8][CH:9]=[C:4]3[C:3]([C:10]([O:12][CH3:13])=[O:11])=[CH:2]2)=[CH:16][CH:17]=1

Participants

10

Reactant 5

HCID 8182DodecaneHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 6094924-IodopyridineHCID 21110084methyl 1H-pyrrolo[2,3-b]pyridine-3-carboxylate

Product 1

HCID 21110086HCID 21110086, compoundYield 67.1%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

1.76 g (10 mmol) of methyl 1H-pyrrolo[2,3-b]pyridine-3-carboxylate, 2.66 g (13 mmol) of 4-iodopyridine, 0.19 g (1 mmol) of copper(1) iodide, 4.46 g (21 mmol) of tripotassium phosphate, 1.2 cm3 of a trans-1,2-cyclohexanediamine (10 mmol) and 0.5 cm3 of n-dodecane were added to 100 cm3 of dioxane under an argon atmosphere at a temperature in the region of 20° C. The mixture was heated at reflux of the solvent for 20 h and then it was rapidly added to a mixture of 300 cm3 of ethyl acetate and 300 cm3 of water. The organic phase was separated by settling, washed 3 times with 300 cm3 of water and then 300 cm3 of saturated aqueous sodium chloride solution, dried over magnesium sulfate and then concentrated to dryness under reduced pressure (2.7 kPa). The residue was purified by flash chromatography on a column of silica gel (0.04–0.06 mm), elution being carried out with a cyclohexane/ethyl acetate (50/50 by volume) mixture. The fractions comprising the expected product were combined and concentrated to dryness under reduced pressure (2.7 kPa) and the residue was triturated in 30 cm3 of diisopropyl ether, filtered off and then dried under a hood. 1.7 g of methyl 1-(pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate were thus obtained in the form of a white powder.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux of the solvent for 20 h
  3. customThe organic phase was separated
  4. washwashed 3 times with 300 cm3 of water
  5. dry with material300 cm3 of saturated aqueous sodium chloride solution, dried over magnesium sulfate
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe residue was purified by flash chromatography on a column of silica gel (0.04–0.06 mm), elution
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  9. customthe residue was triturated in 30 cm3 of diisopropyl ether
  10. filtrationfiltered off
  11. customdried under a hood

Sources & evidence

ORD record
ord-807a3baed0344fa2a78a97c6508525ca
Source dataset
uspto-grants-2007_06
Patent number
US07230007B2

Reaction notes

Loading…