Cesium carbonate → 2-Phenylthiazole

HRID 747928Notes

Reaction equation

HRID 747928 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[C:7]1(B(O)O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:7]1([C:2]2[S:3][CH:4]=[CH:5][N:6]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 764302-Bromothiazole

Product 1

HCID 5474942-PhenylthiazoleYield 70.5%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-bromothiazole (1.0 g, 6.1 mmol, Aldrich) in dioxane (25 mL) was treated with phenylboronic acid (0.82 g, 6.4 mmol), Pd(PtBu3)2 (0.16 g, 0.3 mmol, Strem) and Cs2CO3 (3.97 g, 12.2 mmol). The mixture was stirred at 80° C. for 12 hours. The reaction mixture was cooled to ambient temperature, concentrated under reduced pressure, and purified by column chromatography (SiO2, 1:1 hexanes/ethyl acetate) to give provide the title compound (0.69 g, 4.3 mmol, 70%). 1H NMR (CDCl3, 300 MHz) 67.33 (m, 1H), 7.41-7.48 (m, 3H), 7.87 (d, 1H, J=3.4 Hz), 7.95-8.00 (m, 2H); MS (DCl/NH3) m/z 162 (M+H+).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. custompurified by column chromatography (SiO2, 1:1 hexanes/ethyl acetate)
  4. customto give

Sources & evidence

ORD record
ord-cc4bdef70c124ef9bfdc177a384417c5
Source dataset
uspto-grants-2008_07
Patent number
US07399765B2

Reaction notes

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