4-Toluenesulfonyl chloride → 7-iodo-5-(toluene-4-sulfonyl)-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine

HRID 1677400

Reaktionsgleichung

[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=3)[N:9]=2)[NH:4][CH:3]=1.[H-].[Na+].[CH3:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>C1COCC1>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=3)[N:9]=2)[N:4]([S:32]([C:29]2[CH:30]=[CH:31][C:26]([CH3:25])=[CH:27][CH:28]=2)(=[O:34])=[O:33])[CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

7-Iodo-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine (371 mg, 0.9 mmol) was suspended in 5 ml of THF and cooled to 0° C. in an ice bath. Sodium hydride, 60% dispersion in mineral oil (43 mg, 1.08 mmol) was added and the suspension was stirred for 20 minutes. 4-Methyl-benzenesulfonyl chloride (189 mg, 0.99 mmol) was added, the ice bath was removed, and the reaction was stirred at room temperature for 3 hours. The solvent was evaporated on a rotary evaporator. The residue was triturated with 1M potassium hydroxide. The solid was filtered, washed with water, and dried to yield 480 mg of 7-iodo-5-(toluene-4-sulfonyl)-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine which was used without further purification.

Aufarbeitung

customthe ice bath was removed
stirringthe reaction was stirred at room temperature for 3 hours
customThe solvent was evaporated on a rotary evaporator
customThe residue was triturated with 1M potassium hydroxide
filtrationThe solid was filtered
washwashed with water
customdried

Quellen und Nachweise

ORD-Eintrag: ord-7e90248477c94ec6b75bddd8661369fe
Quelldatensatz: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08008298B2

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