Methyl iodide → 1-methyl-5-nitro-2-phenyl-1H-indole

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Reaction Steps

Sodium hydride (1.1 g, 29.0 mmol) is added to 2-phenyl-5-nitro-1H-indole (Example 5b, 6.5 g, 26.0 mmol) in 100 mL of DMF. The mixture is stirred at room temperature for 1 hour. MeI (1.62 mL, 26.0 mmol) is added dropwise and the mixture is stirred at room temperature for 1 hour. The resulting mixture is poured into H2O/ice and the product is filtered off and washed with H2O. The solid is recrystallized from hexane and filtered off. Yield: 6.5 g (99.7%); Rf (2/1 hexane/ethyl acetate): 0.60; IR (KBr): 3434, 2923, 1515, 1462 cm−1; 1H-NMR (d6-DMSO) 8.50 (d, J=1.5 Hz, 1H); 7.90 (dd, J=8.6 Hz, 1.5 Hz, 1H); 7.80-7.30 (m, 6H); 6.75 (s, 1H); 3.75 (s, 3H).

Provenance & Evidence