4-Fluoroiodobenzene → HCID 46866328, compound

HRID 1913886Notes

Reaction equation

HRID 1913886 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[CH:8]=2)[NH:3]1.[F:26][C:27]1[CH:32]=[CH:31][C:30](I)=[CH:29][CH:28]=1.CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.[Cu](I)I>[F:26][C:27]1[CH:32]=[CH:31][C:30]([N:3]2[C:4]3[C:9](=[CH:8][C:7]([O:12][CH:13]4[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]4)=[CH:6][CH:5]=3)[CH2:10][CH2:11][C:2]2=[O:1])=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 96054-FluoroiodobenzeneHCID 10796Cesium carbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 66683855HCID 66683855, compound

Product 1

HCID 46866328HCID 46866328, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

A suspension of tert-butyl 4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yloxy)piperidine-1-carboxylate prepared in Example 7-(1) (3.0 g), 1-fluoro-4-iodobenzene (2.9 g), rac-trans-N,N′-dimethylcyclohexane-1,2-diamine (1.2 g), copper iodide (0.41 g) and cesium carbonate (5.6 g) in toluene (8.0 mL) was stirred at 100° C. for 4 hours. The reaction mixture was cooled to room temperature, diluted with toluene and filtered to remove insoluble materials. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=7/3 to 1/4) to give the titled compound (3.8 g, 99%) as a colorless amorphous substance.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. customto remove insoluble materials
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=7/3 to 1/4)

Sources & evidence

ORD record
ord-6fff0c25ce3a4c979eb4cd35a7733a2a
Source dataset
uspto-grants-2013_12
Patent number
US08609847B2

Reaction notes

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