Methanesulfonyl chloride → HCID 86594331, compound

Participants

Reaction Conditions

Reaction Steps

[6-(tert-Butyl-dimethyl-silanyloxy)-1H-indol-2-yl]-methanol (2.0 g, 7.21 mmol) is dissolved in DMF (950 ml), cooled to 0° C. TEA (2.01 ml, 14.42 mmol) and MsCl (0.83 g, 7.21 mmol) are added. The mixture is stirred at room temperature for 1 hour. NaN3 (2.34 g, 34 mmol) is added. The reaction is stirred at room temperature for 1 hour and then 80° C. overnight. The mixture is cooled to room temperature, concentrated. The residue is purified by column chromatography (10% ethyl acetate in hexanes) to give 2-Azidomethyl-6-(tert-butyl-dimethyl-silanyloxy)-1H-indole (1.40 g, 64%). 1H NMR (400 MHz, DMSO-d6): δ 11.08 (s, 1H), 7.38 (d, 1H), 6.80 (s, 1H), 6.58 (m, 1H), 6.40 (s, 1H), 4.53 (d, 2H), 0.96 (s, 9H), 0.17 (s, 6H).

Provenance & Evidence