Sodium Chloride → HCID 18679532, compound

HRID 1633703Notes

Reaction equation

HRID 1633703 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][CH:6]=[CH:5]2.[Cl:12][C:13]1[CH:18]=[CH:17][C:16](I)=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[Cl-]>CN1C(=O)CCC1.[Cu]I>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[N:7]([C:16]1[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=1)[CH:6]=[CH:5]2

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 125101-Chloro-4-iodobenzeneHCID 116871455-bromo-6-fluoro-1H-indole

Product 1

HCID 18679532HCID 18679532, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 0.07 g (5 mmol) 5-Bromo-6-fluoro-1H-indole (1, 1-chloro-4-iodobenzene (2.5 g, 10.5 mmol), 250 mg (1.31 mmol) CuI, 80 mg (0.9 mmol) ZnO, and 1.75 g (12.67 mmol) K2CO3 in degassed NMP was stirred at 170° C. during 6 hours in a pressure tube. After cooling to room temperature, the mixture was poured into 50 ml of saturated aqueous NaCl and extracted three times with Et2O. Drying of the combined organic layers with Na2SO4, evaporation of the solvent, and column chromatography on silica gel with CH2Cl2/hexane 1:2 gave 0.98 g (60%) 5-Bromo-1-(4-chloro-phenyl)-6-fluoro-1H-indole as a yellowish-grey solid, MS: 323 (M, 1Cl, 1Br). (Analogously to Jens Perregaard et. al. J. Med. Chem. 1992, 35, 4813-4822.)

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted three times with Et2O
  3. dry with materialDrying of the combined organic layers with Na2SO4, evaporation of the solvent, and column chromatography on silica gel with CH2Cl2/hexane 1:2

Sources & evidence

ORD record
ord-cd5c083d95004c06ac5f8895df1065bb
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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