Dodecane → Methyl 1-(quinolin-8-yl)-1H-pyrrole-3-carboxylate

HRID 1792800Notes

Reaction equation

HRID 1792800 reaction equation
CCCCCCCCCCCC.Br[C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[N:22]=[CH:21][CH:20]=[CH:19]2.[C@@H]1(N)CCCC[C@H]1N.[CH3:32][O:33][C:34]([C:36]1[CH:40]=[CH:39][NH:38][CH:37]=1)=[O:35].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:32][O:33][C:34]([C:36]1[CH:40]=[CH:39][N:38]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:23]=2[N:22]=[CH:21][CH:20]=[CH:19]3)[CH:37]=1)=[O:35]

Participants

8

Reactant 5

HCID 8182DodecaneHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 1401098-BromoquinolineHCID 12361759methyl 1H-pyrrole-3-carboxylate

Product 1

HCID 22024973Methyl 1-(quinolin-8-yl)-1H-pyrrole-3-carboxylateYield 124.1%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

20 mL of 1,4-dioxane, 0.32 mL of n-dodecane, 1.5 g (7.21 mmol) of 8-bromoquinoline and 0.77 mL (6.41 mmol) of trans-1,2-cyclohexanediamine are added at a temperature in the region of 22° C. under an argon atmosphere to 0.8 g (6.39 mmol) of 3-methoxycarbonyl-1H-pyrrole, 3 g (14.13 mmol) of potassium orthophosphate and 0.09 g (0.47 mmol) of copper iodide. After stirring at a temperature in the region of 100° C. for 15 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is diluted with 100 mL of ethyl acetate and the solution obtained is washed with twice 100 mL of water and then with 25 mL of saturated aqueous sodium chloride solution. After separating the phases by settling, the organic phase is dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give 2 g of a brown oil which is purified by flash chromatography [eluent: cyclohexane/ethyl acetate (80/20 by volume)]. After concentrating the fractions under reduced pressure, 0.8 g of a 1/1 (evaluated by NMR) mixture of 3-methoxycarbonyl-1-(quinol-8-yl)-1H-pyrrole and of 8-bromoquinoline is obtained, which mixture is used without further purifications in the following step.

Workup

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. additionThe residue is diluted with 100 mL of ethyl acetate
  3. customthe solution obtained
  4. washis washed with twice 100 mL of water
  5. customAfter separating the phases
  6. dry with materialthe organic phase is dried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-5dc2a4c4c44e428ca878141a5f4b4e65
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

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