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 1835121Notes

Reaction equation

HRID 1835121 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-863f9bd1976140fb9122fca0003e3358
Source dataset
uspto-grants-2004_08
Patent number
US06770642B2

Reaction notes

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