Potassium Carbonate → HCID 18931448, compound

HRID 1598963Notes

Reaction equation

HRID 1598963 reaction equation
[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][C:8]([Br:12])=[CH:9][CH:10]=2)[NH:5][CH2:4][CH2:3]1.I[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu]I.O>[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][C:8]([Br:12])=[CH:9][CH:10]=2)[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 107525207-Bromo-4,4-dimethyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 18931448HCID 18931448, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Conditions

Temperature
185 °C

Procedure

To a solution of 0.19 g (0.78 mmol) of 4,4-dimethyl-1,2,3,4-tetrahydro-7-bromoquinoline and 5.5 g (3.0 mL, 27 mmol) of 4-iodobenzene stirring under argon, were added 0.30 g (2.2 mmol) of potassium carbonate and 0.12 g (0.63 mmol) of copper(I) iodide. The resulting mixture was heated at 185° C. for 96 hours. The reaction was cooled to room temperature, water was added, and the mixture was extracted with methylene chloride (2x). The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to give an oil. The residue was purified by flash chromatography (hexanes) to give the product as a clear oil. PNMR (300 MHz, CDCl3) d 1.33 (6 H, s), 1.84 (2 H, t, J=6.1 Hz), 3.62 (2 H, t, J=6.1 Hz), 6.77 (1 H, d, J=2.0 Hz), 6.81 (1 H, dd, J=8.2, 2.0 Hz), 7.10 (1 H, d, J=8.2 Hz), 7.16-7.23 (3 H, m), 7.39 (2 H, 2 doublets overlapping).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionthe mixture was extracted with methylene chloride (2x)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give an oil
  8. customThe residue was purified by flash chromatography (hexanes)

Sources & evidence

ORD record
ord-f0aee7f0c735488cad194791e21a1aa4
Source dataset
uspto-grants-1998_04
Patent number
US05739338

Reaction notes

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