Potassium Carbonate → 2-(4-Benzo[1,3]dioxol-5-yl-phenoxymethyl)-thiazole-4-carboxylic acid

HRID 2113022Notes

Reaction equation

HRID 2113022 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.[CH2:20]1[O:28][C:27]2[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][C:22]=2[O:21]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[O:21]1[C:22]2[CH:23]=[CH:24][C:25]([C:16]3[CH:15]=[CH:14][C:13]([O:12][CH2:11][C:8]4[S:9][CH:10]=[C:6]([C:4]([OH:3])=[O:5])[N:7]=4)=[CH:18][CH:17]=3)=[CH:26][C:27]=2[O:28][CH2:20]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 576433502-(4-Iodo-phenoxymethyl)-thiazole-4-carboxylic acid ethyl ester2×

Product 1

HCID 116960982-(4-Benzo[1,3]dioxol-5-yl-phenoxymethyl)-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 2-(4-iodo-phenoxymethyl)-thiazole-4-carboxylic acid ethyl ester (of intermediate 2; 75 mg, 0.2 mmol) in dioxane (4 mL) was added to a reaction tube containing 3,4-methylenedioxybenzeneboronic acid (ASDI Incorporated, Newark, Del.; 100 mg, 0.6 mmol). A solution of potassium carbonate (80 mg, 0.6 mmol) in water (0.4 mL) was added and the mixture was degassed. A solution of bis(tricyclohexylphosphine)-palladium (available from Strem Chemicals, Inc., Newburyport, Mass.; 7 mg, 0.01 mmol) in dioxane (0.5 mL) was added and the tube was heated in a microwave oven at 170 degrees for 25 min. The solution was acidified, filtered through silica gel, evaporated, and triturated with aqueous methanol to give 2-(4-benzo[1,3]dioxol-5-yl-phenoxymethyl)-thiazole-4-carboxylic acid. Mass spectrum MH+=356.

Workup

  1. customthe mixture was degassed
  2. temperaturethe tube was heated in a microwave oven at 170 degrees for 25 min
  3. filtrationfiltered through silica gel
  4. customevaporated
  5. customtriturated with aqueous methanol

Sources & evidence

ORD record
ord-6e775657c3374bd095aa9526d04cc23c
Source dataset
uspto-grants-2009_04
Patent number
US07524870B2

Reaction notes

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