Reaktion #53774

Reaktionsgleichung

product

5-(5,6-Difluoro-1H-indol-2-yl)-2-methoxy-phenylamine

5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenylamine

thiophene-2-sulfonyl chloride

pyridine

→

product

Thiophene-2-sulfonic acid [5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-amide

Lösungsmittel

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   workup.WAITto stand 1.75 hours at room temperature
3. 3
   SonstigeThe mixture was partitioned between water (200 mL) and ethyl acetate (200 mL)
4. 4
   Waschenthe organic layer was washed with 1N HCl (100 mL), water (100 mL), and brine (100 mL)
5. 5
   Trocknendried (magnesium sulfate)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated to a purple-tinted solid
8. 8
   SonstigeThe solid was triturated with hexanes/ethyl acetate, 1/1, v/v

Vorschrift

The product from Example 3, 5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenylamine, (0.274 g, 1.0 mmol) was mixed with thiophene-2-sulfonyl chloride (0.192 g, 1.0 mmol) and pyridine (3 mL) was added, and the reaction mixture was heated briefly to 50° C. and then allowed to stand overnight at room temperature. Water (7 mL) was added and the mixture allowed to stand 1.75 hours at room temperature. The mixture was partitioned between water (200 mL) and ethyl acetate (200 mL) and the organic layer was washed with 1N HCl (100 mL), water (100 mL), and brine (100 mL), dried (magnesium sulfate), filtered, and concentrated to a purple-tinted solid. The solid was triturated with hexanes/ethyl acetate, 1/1, v/v to give the product (0.322 g), mp 211-213° C.

Quelle