Benzyl Bromide → Benzyl 4-methoxyindole-2-carboxylate

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Reaction Steps

2.65 g of 4-methoxyindole-2-carboxylic acid are dissolved in 15 ml of DMF, 2.11 g of DBU are added and the mixture is then stirred at RT for 1 hour. 2.61 g of benzyl bromide are added dropwise at RT and this mixture is stirred for 5 hours at RT. The mixture is concentrated under vacuum and the residue is taken up in EtOAc, washed with water, with saturated Na2CO3 solution, with sulphate buffer and then with saturated aqueous NaCl. This solution is dried over Na2SO4 and concentrated. 3.57 g of the expected compound are obtained, which product crystallizes from pentane: m.p.=162-164° C.

Provenance & Evidence