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

HRID 492192Notes

Reaction equation

HRID 492192 reaction equation
CCCCCCCCCCCC.Br[C:14]1[CH:15]=[N:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2.[C@@H]1(N)CCCC[C@H]1N.[CH3:32][O:33][C:34]([C:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[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[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[N:38]([C:14]2[CH:15]=[N:16][C:17]3[C:22]([CH:23]=2)=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:37]=1)=[O:35]

Participants

8

Reactant 5

HCID 8182DodecaneHCID 214133-BromoquinolineHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 589098Methyl indole-3-carboxylate

Product 1

HCID 68972286Methyl 1-(quinolin-3-yl)-1H-indole-3-carboxylateYield 79.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
22 °C

Procedure

5 cm3 of 1,4-dioxane, 230 cm3 of n-dodecane, 1.04 g (5 mmol) of 3-bromoquinoline and 0.6 cm3 (5 mmol) of trans-1,2-cyclohexanediamine are added at 22° C. under an argon atmosphere to 0.876 g (5 mmol) of 3-methoxycarbonyl-1H-indole, 2.23 g (10.51 mmol) of potassium orthophosphate and 0.09 g (0.5 mmol) of copper iodide. After stirring at 100° C. for 31 hours and after 48 hours at 22° C., the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is diluted with 100 cm3 of ethyl acetate and then washed with 3 times 100 cm3 of water and 25 cm3 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 1.2 g of a residue which is purified by flash chromatography [eluent: cyclohexane/ethyl acetate (8/2 by volume)]. After concentrating the fractions under reduced pressure, 0.9 g of a yellow solid is obtained, which solid is recrystallised under hot conditions from a cyclohexane (6 cm3)/ethyl acetate (a few drops) mixture to give, after filtering off and drying under reduced pressure (2.7 kPa) at 40° C., 0.15 g of 3-methoxycarbonyl-1-(quinol-3-yl)-1H-indole in the form of a white solid melting at 138° C.

Workup

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. additionThe residue is diluted with 100 cm3 of ethyl acetate
  3. washwashed with 3 times 100 cm3 of water and 25 cm3 of saturated aqueous sodium chloride solution
  4. customAfter separating the phases
  5. dry with materialthe organic phase is dried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-ef6b0241ff644b84a5367b2bd68e4051
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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