4-Fluoroiodobenzene → HCID 67200683, compound

HRID 1423072Notes

Reaction equation

HRID 1423072 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][NH:9][C:10]=2[CH:11]=[C:12]([Br:14])[CH:13]=1)=[O:4].C([O-])([O-])=O.[K+].[K+].[F:21][C:22]1[CH:27]=[CH:26][C:25](I)=[CH:24][CH:23]=1.CN[C@@H]1CCCC[C@H]1NC>O.[Cu]I.CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][N:9]([C:25]3[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=3)[C:10]=2[CH:11]=[C:12]([Br:14])[CH:13]=1)=[O:4]

Participants

8

Reactant 4

HCID 96054-FluoroiodobenzeneHCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 13770009methyl 6-bromo-1H-indole-4-carboxylate

Product 1

HCID 67200683HCID 67200683, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-bromo-1H-indole-4-carboxylic acid methyl ester (2.00 g, 7.84 mmol), CuI (38.0 mg, 0.20 mmol) and K2CO3 (1.18 g, 8.50 mmol) in a sealed tube is degassed with argon. To the mixture is added 4-fluoroiodobenzene (1.78 g, 8.00 mmol) and trans-N,N′-dimethyl-cyclohexane-1,2-diamine (0.20 g, 1.40 mmol) followed by DMF (25 mL). The reaction mixture is warmed at 120° C. After 3 hours, the reaction is diluted with water and extracted with EtOAc. The combined organic layers are washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with EtOAc-hexanes (20:80) to afford 6-bromo-1-(4-fluorophenyl)-1H-indole-4-carboxylic acid methyl ester.

Workup

  1. customis degassed with argon
  2. extractionextracted with EtOAc
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica gel chromatography
  8. washeluting with EtOAc-hexanes (20:80)

Sources & evidence

ORD record
ord-499083a094a746368de57fa88fa8fb1f
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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