Ethyl Acetate → 3-bromo-2-(ethoxycarbonyl)-1-isobutyl-1H-indole-5-carboxylic acid

HRID 2249694Notes

Reaction equation

[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:11]=[O:12])[CH:9]=2)[N:4]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:3]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18].O.O.P([O-])(O)(O)=[O:25].[Na+].Cl([O-])=O.[Na+].C(OCC)(=O)C>C(#N)C.O.OO>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([OH:25])=[O:12])[CH:9]=2)[N:4]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:3]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

Conditions

Temperature: 60 °C

Procedure

In 7 ml of acetonitrile is dissolved 0.65 g of ethyl 3-bromo-5-formyl-1-isobutyl-1H-indole-2-carboxylate. To the solution are successively added at ambient temperature 1.56 g of sodium dihydrogen-phosphate dihydrate dissolved in 22 ml of water and 0.64 ml of 30% aqueous hydrogen peroxide. Then, 0.68 g of sodium chlorite dissolved in 20 ml of water is dropwise added thereto at 5-10° C. The mixture thus obtained is stirred at 60° C. for one hour. Ethyl acetate and water are added to the reaction mixture, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. Thus, 0.37 g of 3-bromo-2-(ethoxycarbonyl)-1-isobutyl-1H-indole-5-carboxylic acid is obtained as a yellow solid product.

Workup

additionis dropwise added
customat 5-10° C
customThe mixture thus obtained
customthe organic layer is separated
customThe organic layer thus obtained
washis washed with water and saturated aqueous solution of sodium chloride successively
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record: ord-335ce303a31d4215a8775af4f11aeec7
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07314888B1

Reaction notes

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