Tributyltin Chloride → 7-Acetyl-5-methyl-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole

HRID 989821Notes

Reaction equation

HRID 989821 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.[C:16]([C:19]1[N:20]=[C:21]([CH3:27])[N:22]2[CH:26]=[CH:25][S:24][C:23]=12)(=[O:18])[CH3:17].C([Li])CCC.CCCCCC.[CH2:39]([Sn:43](Cl)([CH2:48][CH2:49][CH2:50][CH3:51])[CH2:44][CH2:45][CH2:46][CH3:47])[CH2:40][CH2:41][CH3:42].[Cl-].[NH4+]>C1COCC1>[C:16]([C:19]1[N:20]=[C:21]([CH3:27])[N:22]2[CH:26]=[C:25]([Sn:43]([CH2:44][CH2:45][CH2:46][CH3:47])([CH2:48][CH2:49][CH2:50][CH3:51])[CH2:39][CH2:40][CH2:41][CH3:42])[S:24][C:23]=12)(=[O:18])[CH3:17]

Participants

7

Reactant 5

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 234491157-Acetyl-5-methylimidazo[5,1-b]thiazoleHCID 23714775LiHMDS tetrahydrofuranHCID 178418244HCID 178418244, compound

Product 1

HCID 234491457-Acetyl-5-methyl-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1.0 N lithiumbis(trimethylsilyl)amide/THF solution (3.75 ml) was added dropwise to a solution of 613 mg of 7-acetyl-5-methylimidazo[5,1-b]thiazole in 34 ml of THF in an argon atmosphere at −73° C. The mixture was stirred at the same temperature for 50 min. A 1.59 N n-butyllithium/n-hexane solution (4.71 ml) was added dropwise thereto. The mixture was stirred at the same temperature for 50 min. Tri-n-butylstannyl chloride (1.16 ml) was added dropwise thereto. The mixture was further stirred at the same temperature for 40 min. An ammonium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate and washing with brine. The extract was dried over anhydrous magnesium sulfate and then filtered. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to give 1.40 g of the title compound.

Workup

  1. stirringThe mixture was stirred at the same temperature for 50 min
  2. stirringThe mixture was further stirred at the same temperature for 40 min
  3. extractionfollowed by extraction with ethyl acetate
  4. washwashing with brine
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed by distillation under the reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-979dd5aa34d3465fb7769b103844eef9
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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