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

HRID 1810884Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1810884
[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

5

Edukt 2

HCID 668363-Bromo-4-methoxybenzoic acidHCID 45074056methyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate hydrochloride

Produkt 1

HCID 670763302-(3-Bromo-4-methoxy-benzoylamino)-indane-2-carboxylic acid methyl esterAusbeute 81,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 24386Thionyl ChlorideLösungsmittel

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

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

Quellen und Nachweise

ORD-Eintrag
ord-347b23462a3741fd80c757f355566972
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362073B2

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