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ChemicalBook CAS DataBase List 5-Bromoindole-2-carboxylic acid methyl ester
210345-56-5

5-Bromoindole-2-carboxylic acid methyl ester synthesis

6synthesis methods
-

Yield:-

Reaction Conditions:

Stage #1:5-bromo-2-indolecarboxylic acid with hydrogenchloride in methanol at 20;
Stage #2: with ammonia

Steps:

14 Preparation 14; methyl 5-bromo-1H-indole-2-carboxylate
A solution of 5-Bromo-1H-indole-2-carboxylic acid (commercial, 10.0 g, 41.6 mmol) in methanol (200 ml) was cooled to 0 °C and saturated with HCI (g).. The resulting solution was allowed to warm gradually to room temperature overnight.. The solvent was removed in vacuo and the residue treated with 0.88 ammonia (500 ml).. The resulting solution was extracted with dichloromethane (3-fold 150 ml) and the combined organics dried (magnesium sulphate) and the solvent removed in vacuo to give the required product as a colourless oil (8.35 g).1H NMR (400MHz, CDCl3): δ = 8.96 (1H, bs), 7.83 (1H, s), 7.40 (1H, d), 7.30 (1H, d), 7.14 (1H, s), 3.95 (3H, s). LRMS (electrospray): m/z [M-H]- 252 / 254.

References:

Pfizer Limited EP1460064, 2004, A1 Location in patent:Page 35

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