Thiophene-3-boronic acid → HCID 11529792, compound

HRID 2113034Notes

Reaction equation

HRID 2113034 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16](I)=[CH:15][CH:14]=2)[S:9][CH:10]=1)=[O:5])C.[S:20]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21]1>O1CCOCC1>[S:20]1[CH:24]=[CH:23][C:22]([C:16]2[CH:15]=[CH:14][C:13]([O:12][CH2:11][C:8]3[S:9][CH:10]=[C:6]([C:4]([OH:3])=[O:5])[N:7]=3)=[CH:18][CH:17]=2)=[CH:21]1

Participants

4

Reactant 2

HCID 581760Thiophene-3-boronic acidHCID 576433502-(4-Iodo-phenoxymethyl)-thiazole-4-carboxylic acid ethyl ester2×

Product 1

HCID 11529792HCID 11529792, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-(4-iodo-phenoxymethyl)-thiazole-4-carboxylic acid ethyl ester (of Intermediate 2; 78 mg, 0.2 mmol) in dioxane (2 mL) was degassed with nitrogen and then added to a reaction vial containing thiophene-3-boronic acid (available from Aldrich Chemical Company, Inc., Milwaukee, Wis.). The solution was sonicated and degassed and a solution of potassium carbonate (1.5 M, 0.4 mL) was added, followed by bis(tri-cyclo-hexylphosphine)palladium (available from Strem Chemicals, Inc., Newburyport, Mass.; 7 mg, 0.01 mmol) was added. The mixture was degassed and then heated in a microwave oven at 170 degrees for 25 min. The reaction mixture was evaporated in the Genevac to give 2-(4-thiophen-3-yl-phenoxymethyl)-thiazole-4-carboxylic acid. Mass spectrum MH+=318.

Workup

  1. additionadded to a reaction
  2. customThe solution was sonicated
  3. customdegassed
  4. additiona solution of potassium carbonate (1.5 M, 0.4 mL) was added
  5. additionwas added
  6. customThe mixture was degassed
  7. temperatureheated in a microwave oven at 170 degrees for 25 min
  8. customThe reaction mixture was evaporated in the Genevac

Sources & evidence

ORD record
ord-95ed1d5d76b1454482865184c8a96e91
Source dataset
uspto-grants-2009_04
Patent number
US07524870B2

Reaction notes

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