Potassium Carbonate → HCID 18971807, compound

HRID 2395408Notes

Reaction equation

HRID 2395408 reaction equation
[C:1]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)([O:3][CH3:4])=[O:2].[C:14](=[O:17])([O-])[O-].[K+].[K+].CN1[CH2:25][CH2:24][CH2:23][C:22]1=[O:26]>C(OCC)(=O)C.O>[CH:23]12[CH2:6][CH:5]([CH2:25][CH2:24]1)[CH2:1][CH:22]2[O:26][C:8]1[CH:9]=[C:10]([N:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:5]([C:1]([O:3][CH3:4])=[O:2])=[CH:6]2)[CH:11]=[CH:12][C:13]=1[O:17][CH3:14]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 589098Methyl indole-3-carboxylate

Product 1

HCID 18971807HCID 18971807, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of (1.0 g, 5.71 mmol, 1.0 eq) 3-carbomethoxy indole, (2.21 g, 7.42 mmol, 1.3 eq) (±)-1-methoxy-2-exo-norbornyloxy-4-bromobenzene (30.7 mg, 0.107 mmol, 0.2 eq) cuprous bromide, and (866 mg, 6.27 mmol, 1.1 eq) potassium carbonate in 15 ml of 1-methyl-2-pyrrolidinone was heated to 150° C. for 24 hours. The reaction mixture was cooled, diluted with 350 ml of ethyl acetate and 350 ml of H2O, and the layers separated. The aqueous layer was extracted twice with ethyl acetate. The ethyl acetate extracts were combined, washed twice with H2O, once with brine, dried over Na2SO4 and concentrated in vacuo to give a light brown oil. Silica gel chromatography eluting with 20% ethyl acetatehexane gave 1.05 g, 47%, of a white foamy solid. M.P.: 120°-122° C. Elemental Analysis Calc'd for C24H25NO4 : Calc'd: C, 73.64; H, 6.44; N, 3.58. Found: C, 73.70; H, 6.37; N, 3.59.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted twice with ethyl acetate
  4. washwashed twice with H2O, once with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customto give a light brown oil
  8. washSilica gel chromatography eluting with 20% ethyl acetatehexane
  9. customgave 1.05 g, 47%

Sources & evidence

ORD record
ord-9d5dcb0f07c5466eb500b19719a1c109
Source dataset
uspto-grants-1998_09
Patent number
US05814651

Reaction notes

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