6-Chloroimidazo(2,1-b)(1,3)thiazole-5-sulfonyl chloride → 3-(3-Azidopropyl)-1-[(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl]-5-fluoro-1H-indole

HRID 1793865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1793865
[N:1]([CH2:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:16])[CH:14]=2)[NH:9][CH:8]=1)=[N+:2]=[N-:3].CC([O-])(C)C.[K+].[Cl:23][C:24]1[N:25]=[C:26]2[N:30]([C:31]=1[S:32](Cl)(=[O:34])=[O:33])[CH:29]=[CH:28][S:27]2>C1COCC1>[N:1]([CH2:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:16])[CH:14]=2)[N:9]([S:32]([C:31]2[N:30]3[C:26]([S:27][CH:28]=[CH:29]3)=[N:25][C:24]=2[Cl:23])(=[O:33])=[O:34])[CH:8]=1)=[N+:2]=[N-:3]

Komponenten

5

Edukt 3

HCID 27997176-Chloroimidazo(2,1-b)(1,3)thiazole-5-sulfonyl chlorideHCID 113449903-(3-azidopropyl)-5-fluoro-1H-indoleHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 222197373-(3-Azidopropyl)-1-[(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl]-5-fluoro-1H-indoleAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred solution of 3-(3-azidopropyl)-5-fluoro-1H-indole (150 mg, 0.53 mmol) in THF is treated with KOt-Bu (0.55 ml, 0.55 mmol, 1M in THF solution) under nitrogen at room temperature, stirred for 30 min, treated with 6-chloroimidazo[2,1-b]thiazole-5-sulfonylchloride (141 mg, 0.55 mmol), stirred for 18 h at room temperature, quenched with 1N HCl and water and diluted with EtOAc. The two phases are separated and the aqueous phase is extracted with EtOAc. The extracts are combined with the organic phase and are dried over MgSO4 and concentrated in vacuo. The resultant residue is purified by flash chromatography (silica gel, EtOAc/hexane: 3/7) to give the title product as a yellow solid, 203 mg (88% yield), mp 84–86° C., identified by NMR and mass spectral analyses.

Aufarbeitung

  1. stirringstirred for 18 h at room temperature
  2. customquenched with 1N HCl and water
  3. additiondiluted with EtOAc
  4. customThe two phases are separated
  5. extractionthe aqueous phase is extracted with EtOAc
  6. dry with materialare dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue is purified by flash chromatography (silica gel, EtOAc/hexane: 3/7)

Quellen und Nachweise

ORD-Eintrag
ord-d19d3c2b25df42a3bc26a12453e533f7
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07022701B2

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