Tributyltin Chloride → HCID 23449013, compound

HRID 1839320Notes

Reaction equation

HRID 1839320 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][C:7]([C:9]1[N:10]=[CH:11][N:12]2[CH:16]=[CH:15][S:14][C:13]=12)=[O:8])(=[O:4])=[O:3].[CH2:17]([Sn:21](Cl)([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH3:20].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.C([Li])CCC.CCCCCC.[Cl-].[NH4+]>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[CH3:1][S:2]([NH:5][CH2:6][C:7]([C:9]1[N:10]=[CH:11][N:12]2[CH:16]=[C:15]([Sn:21]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:17][CH2:18][CH2:19][CH3:20])[S:14][C:13]=12)=[O:8])(=[O:3])=[O:4]

Participants

8

Reactant 5

HCID 15096Tributyltin Chloride2×HCID 25517Ammonium ChlorideHCID 23449274HCID 23449274, compoundHCID 23714775LiHMDS tetrahydrofuranHCID 178418244HCID 178418244, compound2×

Product 1

HCID 23449013HCID 23449013, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

7-Methanesulfonylaminoacetylimidazo[5,1-b]thiazole (46.2 mg) was dissolved in 2 ml of THF and 0.4 ml of HMPA. Tri-n-butylstannyl chloride (0.076 ml) and 0.713 ml of a 1.0 N lithiumbis(trimethylsilyl)amide/THF solution were added dropwise in that order to the solution in an argon atmosphere at −70° C. The mixture was stirred at the same temperature for 1.5 hr. A 1.59 N n-butyllithium/n-hexane solution (0.146 ml) was added dropwise thereto. The mixture was stirred at the same temperature for one hr. A 1.59 N n-butyllithium/n-hexane solution ((0.146 ml) and 0.076 ml of tri-n-butylstannyl chloride were added dropwise thereto. The mixture was stirred at the same temperature for 45 min. An ammonium chloride solution was added to the reaction solutions, followed by extraction with ethyl acetate. The organic layer was washed twice with brine, dried over anhydrous magnesium sulfate, and 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 37.5 mg of the title compound.

Workup

  1. stirringThe mixture was stirred at the same temperature for one hr
  2. stirringThe mixture was stirred at the same temperature for 45 min
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed twice with brine
  5. dry with materialdried 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-bfaa9e13568549c192c77d1c1c478eb7
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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