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

HRID 25504

Reaktionsgleichung

Reaktionsgleichung von HRID 25504
[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.[N+:21]([C:24]1[CH:25]=[C:26]([S:30](Cl)(=[O:32])=[O:31])[CH:27]=[CH:28][CH:29]=1)([O-:23])=[O:22].N1C=CC=CC=1>O>[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]([NH:18][S:30]([C:26]3[CH:27]=[CH:28][CH:29]=[C:24]([N+:21]([O-:23])=[O:22])[CH:25]=3)(=[O:31])=[O:32])[CH:17]=1)=[CH:5]2

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 99434395-(5,6-difluoro1H-indol-2-yl)-2-methoxy-phenylamine2×

Produkt 1

HCID 10298171N-[5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-3-nitro-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 (0.548 g, 2.0 mmol), was mixed with 3-nitrobenzenesulfonyl chloride (0.466 g, 2.0 mmol) and pyridine (9 mL) was added, and the reaction mixture was heated briefly to 50° C. and then allowed to stand overnight at room temperature. Water (15 mL) was added and the mixture allowed to stand 1.5 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 yellow solid. The solid was triturated with hexanes/ethyl acetate, 1/1, dried in vacuo, taken up in tetrahydrofuran, concentrated to dryness, triturated with hexanes/ethyl acetate, 4/1, v/v and was collected by filtration (0.488 g), mp 228-230° C.

Aufarbeitung

  1. additionwas added
  2. waitto stand 1.5 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 yellow solid
  8. customThe solid was triturated with hexanes/ethyl acetate, 1/1
  9. customdried in vacuo
  10. concentrationconcentrated to dryness
  11. customtriturated with hexanes/ethyl acetate, 4/1, v/v
  12. filtrationwas collected by filtration (0.488 g), mp 228-230° C.

Quellen und Nachweise

ORD-Eintrag
ord-11d68fa41b3641f5be27cc478961e91c
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858739B2

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