2-Bromothiazole → HCID 819109, compound

HRID 1919173Notes

Reaction equation

HRID 1919173 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C([Sn](CCCC)(CCCC)[C:12]1[S:13][CH:14]=[CH:15][N:16]=1)CCC>C1(C)C=CC=CC=1>[S:3]1[CH:4]=[CH:5][N:6]=[C:2]1[C:12]1[S:13][CH:14]=[CH:15][N:16]=1

Participants

4

Reactant 2

HCID 764302-BromothiazoleHCID 27632592-(Tributylstannyl)-1,3-thiazole

Product 1

HCID 819109HCID 819109, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
125 °C

Procedure

A solution of 2-bromothiazole (2.85 g, 17.4 mmol), 2-(tributylstannyl)thiazole (5.00 g, 13.4 mmol) and tetrakistriphenylphosphine palladium (0.77 g, 0.67 mmol) in toluene (120 mL) was degassed under vacuum for several minutes, backfilled with nitrogen and heated in a sealed pressure vessel at 125° C. for 48 h. The crude reaction mixture was concentrated and the residue was purified by column chromatography (0 to 30% ethyl acetate/hexanes) to yield 2,2′-bithiazole (2.21 g, 12.5 mmol, 93% yield) as a white solid.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated
  3. customthe residue was purified by column chromatography (0 to 30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-89e147f52cfd481fbeed44238bd0bba6
Source dataset
uspto-grants-2013_12
Patent number
US08618153B2

Reaction notes

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