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Triethyltin bromide → 2-Methyl-4-triethylstannyl-thiazole

HRID 2220119
Notes
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Reaction equation

HRID 2220119 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5](Br)[N:6]=1.C([Li])CCC.[CH2:13]([Sn:15](Br)([CH2:18][CH3:19])[CH2:16][CH3:17])[CH3:14]>CCOCC>[CH3:1][C:2]1[S:3][CH:4]=[C:5]([Sn:15]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:13][CH3:14])[N:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 17701Triethyltin bromideHCID 27631864-Bromo-2-methyl-1,3-thiazoleHCID 178418339Butyllithium

Product 1

HCID 689777192-Methyl-4-triethylstannyl-thiazole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (1.6M, 3.3 mL, 5.35 mmol) was added to a solution of 2,4-dibromothiazole (1.0 g, 4.12 mmol) in anhydrous ether (10 mL) stirred at −78 ° C. under nitrogen. After 20 minutes, methyl trifluromethanesulfonate (878 mg, 5.35 mmol) was added, then the reaction mixture was allowed to warm to room temperature, and stirred for another 1 h. The mixture was quenched and washed with water, washed with brine, dried through MgSO4, and then the solvent was evaporated to give a brown oily residue of 2-methyl-4-bromo-thiazole (900 mg). Under nitrogen, the 2-methyl-4-bromo-thiazole (430 mg, 2.42 mmol) dissolved in anhydrous ether (5 mL) then cooled to −78° C. under nitrogen. n-Butyllithium (1.6M, 1.7 mL, 2.66 mmol) was added, followed, after 10 min by triethylstannyl bromide (760 mg, 2.66 mmol). The solution was then warmed to room temperature, and stirred for another 1 h. The mixture was quenched, and washed with 1N sodium hydroxide, dried through MgSO4, and then the solvent was evaporated to give the sub-title compound give as a brown oily residue (655 mg), which was used without further purification in the next step.

Workup

  1. temperatureThe solution was then warmed to room temperature
  2. customThe mixture was quenched
  3. washwashed with 1N sodium hydroxide
  4. dry with materialdried through MgSO4
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0b272f7fd4a84741bfc9a56ac4cb5921
Source dataset
uspto-grants-2008_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07417050B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes