Benzyl Bromide → 3-(1-Benzyl-6-bromo-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester

HRID 1466772

Reaktionsgleichung

[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Br:20])=[CH:17][CH:18]=3)[NH:13][C:12]=2[CH3:21])[CH:5]=1.[H-].[Na+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Br:20])=[CH:17][CH:18]=3)[N:13]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:12]=2[CH3:21])[CH:5]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

3(6-Bromo-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester (1.13 g, 3.0 mmol) was dissolved in DMF and cooled to 0° C. then sodium hydride (60% dispersion in mineral oil, 0.156 g, 3.9 mmol) was added. After 5 minutes benzyl bromide (0.500 mL, 4.2 mmol) was added and the reaction was allowed to warm to room temperature. After 1 hour the reaction was re-cooled to 0° C. then quenched with aqueous HCl (5 mL, 1N). After extraction the crude product was purified by silica gel chromatography (0-30% EtOAc in hexanes) to afford the title compound.

Aufarbeitung

temperatureto warm to room temperature
temperatureAfter 1 hour the reaction was re-cooled to 0° C.
customthen quenched with aqueous HCl (5 mL, 1N)
extractionAfter extraction the crude product
customwas purified by silica gel chromatography (0-30% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-a0e08480c7d646eeaa46f491ecb06565
Quelldatensatz: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09000025B2

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