Cyclohexanone → Ethyl 1-(3-(naphthalen-1-yloxy)propyl)-4-(2-oxocyclohexyl)-1h-indole-2-carboxylate

HRID 533258Notes

Reaction equation

HRID 533258 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:6]2[CH2:11][CH2:12][CH2:13][O:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.[C:30]1(=[O:36])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[C:15]1([O:14][CH2:13][CH2:12][CH2:11][N:6]2[C:7]3[C:3](=[C:2]([CH:31]4[CH2:32][CH2:33][CH2:34][CH2:35][C:30]4=[O:36])[CH:10]=[CH:9][CH:8]=3)[CH:4]=[C:5]2[C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1

Participants

9

Reactant 4

HCID 7967CyclohexanoneHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 67316436HCID 67316436, compound

Product 1

HCID 67315704Ethyl 1-(3-(naphthalen-1-yloxy)propyl)-4-(2-oxocyclohexyl)-1h-indole-2-carboxylate

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of EXAMPLE 106B (438 mg) and cyclohexanone (196 mg) in dioxane (3 ml) was added tris(dibenzylideneacetone)dipalladium(0) (5 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos, 7 mg) and Cs2CO3 (652 mg). The mixture was stirred at 80° C. under nitrogen overnight. After cooling, the reaction mixture was diluted with ethyl acetate and shaken with water. The product was extracted with ether (200 ml×3). The combined organic extracts were washed with water, brine, and dried over Na2SO4. After filtration, concentration of the mixture and flash column purification (3% ethyl acetate in hexane) provided EXAMPLE 106C.

Workup

  1. temperatureAfter cooling
  2. extractionThe product was extracted with ether (200 ml×3)
  3. washThe combined organic extracts were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration, concentration of the mixture and flash column purification (3% ethyl acetate in hexane)
  6. customprovided EXAMPLE 106C

Sources & evidence

ORD record
ord-71249f500298463da5c2b1c6c39cc121
Source dataset
uspto-grants-2014_10
Patent number
US08853209B2

Reaction notes

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