Tributyltin Chloride → 7-(2-t-Butyldimethylsilyloxyethyl)thio-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole

HRID 1840424Notes

Reaction equation

HRID 1840424 reaction equation
[CH2:1]([Sn:5](Cl)([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.[Si:30]([O:37][CH2:38][CH2:39][S:40][C:41]1[N:42]=[CH:43][N:44]2[CH:48]=[CH:47][S:46][C:45]=12)([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31].[Cl-].[NH4+]>C1COCC1>[Si:30]([O:37][CH2:38][CH2:39][S:40][C:41]1[N:42]=[CH:43][N:44]2[CH:48]=[C:47]([Sn:5]([CH2:10][CH2:11][CH2:12][CH3:13])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:1][CH2:2][CH2:3][CH3:4])[S:46][C:45]=12)([C:33]([CH3:36])([CH3:34])[CH3:35])([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 178368967-(2-t-Butyldimethylsilyloxyethyl)thioimidazo[5,1-b]thiazoleHCID 23714775LiHMDS tetrahydrofuran

Product 1

HCID 178368917-(2-t-Butyldimethylsilyloxyethyl)thio-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tri-n-butylstannyl chloride (1.79 ml) and 13.2 ml of a 1.0 N lithiumbis(trimethylsilyl)amide/THF solution were added to a solution of 1.734 g of 7-(2-t-butyldimethylsilyloxyethyl)thioimidazo[5,1-b]thiazole in 60 ml of THF at −40° C. under an argon atmosphere, and the mixture was stirred at that temperature for one hr. An aqueous ammonium chloride solution was added to the reaction solution. The mixture was extracted with ethyl acetate, followed by washing with brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1) to prepare 2.784 g of the title compound.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washby washing with brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was then removed by distillation
  5. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1)
  6. customto prepare 2.784 g of the title compound

Sources & evidence

ORD record
ord-a3ece466347c428699b6686bacdd9871
Source dataset
uspto-grants-2004_01
Patent number
US06680313B2

Reaction notes

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