Pyridine → 3,5-Dichloro-N-[5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-benzenesulfonamide

HRID 25495

Reaktionsgleichung

Reaktionsgleichung von HRID 25495
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6]([C:12]1[CH:13]=[CH:14][C:15]([O:19][CH3:20])=[C:16]([NH2:18])[CH:17]=1)=[CH:5]2.[Cl:21][C:22]1[CH:23]=[C:24]([S:29](Cl)(=[O:31])=[O:30])[CH:25]=[C:26]([Cl:28])[CH:27]=1.N1C=CC=CC=1>O>[Cl:28][C:26]1[CH:25]=[C:24]([S:29]([NH:18][C:16]2[CH:17]=[C:12]([C:6]3[NH:7][C:8]4[C:4]([CH:5]=3)=[CH:3][C:2]([F:1])=[C:10]([F:11])[CH:9]=4)[CH:13]=[CH:14][C:15]=2[O:19][CH3:20])(=[O:30])=[O:31])[CH:23]=[C:22]([Cl:21])[CH:27]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 5223883,5-Dichlorobenzenesulfonyl chlorideHCID 99434395-(5,6-difluoro1H-indol-2-yl)-2-methoxy-phenylamine2×

Produkt 1

HCID 102996323,5-Dichloro-N-[5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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 3,5-dichlorobenzenesulfonyl chloride (0.256 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 2 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 (0.355 g), mp 217-219° C.

Aufarbeitung

  1. additionwas added
  2. waitto stand 2 hours at room temperature
  3. customThe mixture was partitioned between water (200 mL) and ethyl acetate (200 mL)
  4. washthe organic layer was washed with 1N HCl (100 mL), water (100 mL), and brine (100 mL)
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated to a purple-tinted solid
  8. customThe solid was triturated with hexanes/ethyl acetate, 1/1, v/v

Quellen und Nachweise

ORD-Eintrag
ord-f5d15fd5ce7c4bd0ab9fc741344a9428
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858739B2

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