Hydrochloric Acid → 2-([1,1';3',1'']Terphenyl-4-yloxymethyl)-thiazole-4-carboxylic acid

HRID 2113024Notes

Reaction equation

HRID 2113024 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.[C:20]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:25]=[CH:24][CH:23]=[C:22](B(O)O)[CH:21]=1.C(=O)([O-])[O-].[K+].[K+].Cl>O1CCOCC1.O>[C:16]1([C:31]2[CH:32]=[CH:33][CH:34]=[C:29]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:30]=2)[CH:15]=[CH:14][C:13]([O:12][CH2:11][C:8]2[S:9][CH:10]=[C:6]([C:4]([OH:3])=[O:5])[N:7]=2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2734315(3-Phenylphenyl)boronic acidHCID 576433502-(4-Iodo-phenoxymethyl)-thiazole-4-carboxylic acid ethyl ester2×

Product 1

HCID 116107552-([1,1';3',1'']Terphenyl-4-yloxymethyl)-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; 71 mg, 0.2 mmol) in dioxane (3.5 mL) was added to a reaction tube containing biphenyl-3-boronic acid (available from Lancaster Synthesis Ltd., Morecambe, UK; 119 mg, 0.6 mmol). A solution of potassium carbonate (74 mg, 0.5 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. Concentrated hydrochloric acid (0.1 mL) was added and the mixture was passed through a silica gel column (1 g of silica), and washed with dimethylacetamide (2×1 mL). The filtrate was evaporated to dryness and the resulting gum was triturated twice with 50% aqueous methanol to give 2-([1,1′;3′,1″]terphenyl-4-yloxymethyl) -thiazole-4-carboxylic acid. Mass spectrum MH+=388

Workup

  1. customthe mixture was degassed
  2. temperaturethe tube was heated in a microwave oven at 170 degrees for 25 min
  3. washwashed with dimethylacetamide (2×1 mL)
  4. customThe filtrate was evaporated to dryness
  5. customthe resulting gum was triturated twice with 50% aqueous methanol

Sources & evidence

ORD record
ord-7665b823b1e3422d940ae226a7ba0782
Source dataset
uspto-grants-2009_04
Patent number
US07524870B2

Reaction notes

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