Pyridine → 4-Ethanesulfonylamino-3-methyl-benzofuran-2-carboxylic acid ethyl ester

HRID 29304

Reaktionsgleichung

Reaktionsgleichung von HRID 29304
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[CH2:17]([S:19](Cl)(=[O:21])=[O:20])[CH3:18].N1C=CC=CC=1>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][S:19]([CH2:17][CH3:18])(=[O:21])=[O:20])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 11667Ethanesulfonyl chlorideHCID 687122774-Amino-3-methyl-benzofuran-2-carboxylic acid ethyl ester

Produkt 1

HCID 687119104-Ethanesulfonylamino-3-methyl-benzofuran-2-carboxylic acid ethyl esterAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To 4-amino-3-methyl-benzofuran-2-carboxylic acid ethyl ester (563 mg, 2.57 mmol, 1 eq., prepared according to Example 60, Step 1), CH2Cl2 (12 mL) was added under argon and the reaction was cooled to <0° C. Then ethanesulfonyl chloride (243 uL, 2.57 mmol, 1 eq.), and pyridine (623 uL, 7.70 mmol, 3 eq.) were added and the reaction was stirred while slowly warming to room temperature. After work-up and flash column chromatography, 4-ethanesulfonylamino-3-methyl-benzofuran-2-carboxylic acid ethyl ester was obtained in 69% yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.3 (m, 6 H) 2.8 (s, 3 H) 3.2 (q, J=7.3 Hz, 2 H) 4.4 (m, J=7.1, 7.1, 7.1 Hz, 2 H) 7.2 (d, J=7.6 Hz, 1 H) 7.5 (m, 1 H) 7.6 (m, 1 H) 9.6 (s, 1 H).

Aufarbeitung

  1. temperaturethe reaction was cooled to <0° C

Quellen und Nachweise

ORD-Eintrag
ord-1b3ab73a18504bd78117dd37c87de834
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420001B2

Verknüpfte Notizen

Wird geladen…