Water → 7-(2-Methoxycarbonylvinyl)-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole

HRID 1839315Notes

Reaction equation

HRID 1839315 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.[CH3:30][O:31][C:32]([CH:34]=[CH:35][C:36]1[N:37]=[CH:38][N:39]2[CH:43]=[CH:42][S:41][C:40]=12)=[O:33].O>C1COCC1>[CH3:30][O:31][C:32]([CH:34]=[CH:35][C:36]1[N:37]=[CH:38][N:39]2[CH:43]=[C:42]([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:41][C:40]=12)=[O:33]

Participants

6

Reactant 4

HCID 962WaterHCID 15096Tributyltin ChlorideHCID 23714775LiHMDS tetrahydrofuranHCID 699303387-(2-Methoxycarbonylvinyl)imidazo[5,1-b]thiazole

Product 1

HCID 699279727-(2-Methoxycarbonylvinyl)-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tri-n-butylstannyl chloride (250 μl) and 2.1 ml of a 1.0 N lithiumbis(trimethylsilyl)amide/THF solution were added in that order to a solution of 7-(2-methoxycarbonylvinyl)imidazo[5,1-b]thiazole (a mixture of geometrical isomers) in dry THF in an argon atmosphere at −78° C. The mixture was stirred at the same temperature for 15 min. Water was added thereto. The mixture was extracted with ethyl acetate, followed by washing with saturated 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=4:1) to give 408 mg of the title compound.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washby washing with saturated brine
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-59b08b8dec214cc8b9e9c08f503ae8bb
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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