Reaktion #1483065

Reaktionsgleichung

1H-indole-6-carboxylic acid methyl ester

cyclohexylmethyl bromide

sodium hydride

→

1-cyclohexylmethyl-1H-indole-6-carboxylic acid methyl ester

Ausbeute 74.0%

Lösungsmittel

water

ethyl acetate

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthe organic layer was washed again with dilute NaHCO3 (25 mL)
2. 2
   TrocknenThe organic layer was dried over Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated

Vorschrift

To a solution of commercially available 1H-indole-6-carboxylic acid methyl ester (0.35 g, 2.0 mmol) and cyclohexylmethyl bromide (0.31 mL, 2.2 mmol) in DMF (2 mL) was added sodium hydride (92 mg, 2.3 mmol). After stirring at room temperature for 3 hr, the solution was diluted with water (25 mL) and ethyl acetate (75 mL), the organic layer was washed again with dilute NaHCO3 (25 mL) and then brine (25 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The remaining residue was subjected to flash chromatography (ethyl acetate/hexane, 1:24) to provide 1-cyclohexylmethyl-1H-indole-6-carboxylic acid methyl ester as a white solid (0.40 g, 74% yield). 1H NMR (400 MHz, DMSO) δ 8.10 (s, 1H), 7.62 (m, 2W), 7.58 (d, 1H, J=3.1 Hz), 6.52 (d, 1H, J=3.1 Hz), 4.10 (d, 2H, J=7.4 Hz), 3.85 (s, 3H), 1.77 (m, 1H), 1.65-1.57 (m 3H), 1.46 (m, 2H), 1.19 (m, 3H), 0.98 (m, 2H).

Quelle