3-(2-Bromoethyl)indole → 3-(2-Bromoethyl)-1-(6-chloroimidazo[2,1-b]thiazole-5-sulfonyl)indole

HRID 1835113Notes

Reaction equation

HRID 1835113 reaction equation
[Br:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[Cl:13][C:14]1[N:15]=[C:16]2[N:20]([C:21]=1[S:22](Cl)(=[O:24])=[O:23])[CH:19]=[CH:18][S:17]2.CC(C)([O-])C.[K+]>C1COCC1>[Br:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([S:22]([C:21]2[N:20]3[C:16]([S:17][CH:18]=[CH:19]3)=[N:15][C:14]=2[Cl:13])(=[O:23])=[O:24])[CH:5]=1

Participants

5

Reactant 3

HCID 769243-(2-Bromoethyl)indoleHCID 27997176-Chloroimidazo(2,1-b)(1,3)thiazole-5-sulfonyl chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 112593493-(2-Bromoethyl)-1-(6-chloroimidazo[2,1-b]thiazole-5-sulfonyl)indoleYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(2-bromoethyl)indole (1.0 g, 4.46 mmol) and 6-chloroimidazo[2,1-b]thiazole-5-sulfonyl chloride (0.96 g, 1.1 eq.) in THF is treated with potassium t-butoxide (0.48 g, 1.1 equiv.) at room temperature, stirred for 16 h, quenched with saturated NaHCO3 and extracted with EtOAc. The extracts are combined, dried over MgSO4 and concentrated in vacuo to give the title product as a brown oil, 1.2 g (58% yield), identified by HPLC and mass spectral analyses.

Workup

  1. customquenched with saturated NaHCO3
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c31d52117e2466ea1e8d202eb25264e
Source dataset
uspto-grants-2004_08
Patent number
US06770642B2

Reaction notes

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