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

HRID 492201Notes

Reaction equation

HRID 492201 reaction equation
CCCCCCCCCCCC.I[C:14]1[N:15]=[CH: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[N:15]=[CH: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 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 589098Methyl indole-3-carboxylateHCID 6409703-iodoisoquinoline

Product 1

HCID 68970562Methyl 1-(isoquinolin-3-yl)-1H-indole-3-carboxylateYield 156.9%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

25 cm3 of 1,4-dioxane, 0.256 cm3 of n-dodecane, 1.25 g (4.9 mmol) of 3-iodoisoquinoline and 0.582 cm3 (4.85 mmol) of trans-1,2-cyclohexanediamine are added at a temperature in the region of 22° C. under an argon atmosphere to 0.850 g (4.85 mmol) of 3-methoxycarbonyl-1H-indole, 2.2 g (10.36 mmol) of potassium orthophosphate and 0.085 g (0.45 mmol) of copper iodide. After stirring at a temperature in the region of 100° C. for 17 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is diluted with 100 cm3 of dichloromethane, the suspension obtained is filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa) to give 2.3 g of a brown oil which is purified by flash chromatography [eluent: cyclohexane/ethyl acetate (85/15 by volume)]. After concentrating the fractions under reduced pressure, 1.1 g of 3-methoxycarbonyl-1-(isoquinol-3-yl)-1H-indole are obtained in the form of a white solid. Mass spectrum (EI): El: m/e 302 (M+·), m/e 271.

Workup

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. additionThe residue is diluted with 100 cm3 of dichloromethane
  3. customthe suspension obtained
  4. filtrationis filtered
  5. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-8e79c76335c54a01b5a128e5ef3fd18c
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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