4-Fluoroiodobenzene → HCID 67200683, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence