4-Methoxycarbonylphenylboronic acid → 4-Thiazol-4-yl-benzoic acid methyl ester

HRID 646404Notes

Reaction equation

HRID 646404 reaction equation
Br[C:2]1[N:3]=[CH:4][S:5][CH:6]=1.[CH3:7][O:8][C:9]([C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1)=[O:10]>O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:7][O:8][C:9](=[O:10])[C:11]1[CH:16]=[CH:15][C:14]([C:2]2[N:3]=[CH:4][S:5][CH:6]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 2

HCID 27343694-Methoxycarbonylphenylboronic acidHCID 27632184-Bromothiazole

Product 1

HCID 592646784-Thiazol-4-yl-benzoic acid methyl esterYield 45%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 4-bromothiazole (1.13 g, 6.89 mmol), 4-methoxycarbonylphenylboronic acid (1.85 g, 10.3 mmol) and Tetrakis (triphenylphosphine) palladium (0) (0.35 g, 0.30 mmol) in dioxane (45 mL) and 2M Na2CO3 (17.2 mL) is heated to reflux for 18 h. The reaction is allowed to cool and filtered. The filtrate is evaporated in vacuo, and the residue is dissolved in ethyl acetate and washed with water (2×) and brine (2×). The combined organic layers are dried over Na2SO4, and concentrated in vacuo. The crude material is purified by flash chromatography (100% hexanes-40% ethyl acetate/hexanes) to give 4-thiazol-4-yl-benzoic acid methyl ester as a white solid (0.68 g, 45%) MS (ES+) 220.2

Workup

  1. temperatureis heated
  2. temperatureto reflux for 18 h
  3. temperatureto cool
  4. filtrationfiltered
  5. customThe filtrate is evaporated in vacuo
  6. dissolutionthe residue is dissolved in ethyl acetate
  7. washwashed with water (2×) and brine (2×)
  8. dry with materialThe combined organic layers are dried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe crude material is purified by flash chromatography (100% hexanes-40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ffe38e277e3c41359e313f7110b4b9a9
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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