3-Bromo-4-methoxybenzoic acid → 2-(3-Bromo-4-methoxy-benzoylamino)-indane-2-carboxylic acid methyl ester

HRID 2094711

Reaktionsgleichung

[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=O.Cl.[CH3:14][O:15][C:16]([C:18]1([NH2:27])[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19]1)=[O:17]>S(Cl)(Cl)=O.C(Cl)Cl>[CH3:14][O:15][C:16]([C:18]1([NH:27][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:2]([Br:1])[CH:3]=2)[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19]1)=[O:17]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

3-Bromo-4-methoxybenzoic acid (22.8 g, 98.8 mmol) was dissolved in thionyl chloride (42 ml) and stirred at 60° C. for 30 min. The volatiles were evaporated in vacuo and the residue was stripped with dioxane. The obtained acid chloride was dissolved in DCM (50 ml). 2-Amino-indane-2-carboxylic acid methyl ester hydrochloride (15.0 g, 65.9 mmol) was suspended in DCM (100 ml), EDIA (10.2 g, 79.1 mmol) was added, the mixture was cooled in an ice bath, and the solution of the acid chloride was slowly added. The mixture was stirred overnight at room temperature and evaporated to dryness. The residue was purified by silica gel chromatography (DCM/methanol gradient) and subsequent crystallization from EA to give 21.8 g of the title compound.

Aufarbeitung

customThe volatiles were evaporated in vacuo
dissolutionThe obtained acid chloride was dissolved in DCM (50 ml)
additionEDIA (10.2 g, 79.1 mmol) was added
temperaturethe mixture was cooled in an ice bath
stirringThe mixture was stirred overnight at room temperature
customevaporated to dryness
customThe residue was purified by silica gel chromatography (DCM/methanol gradient) and subsequent crystallization from EA

Quellen und Nachweise

ORD-Eintrag: ord-b2e746e2f2054cbd8d1762945a560a71
Quelldatensatz: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08445530B2

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