2-Bromothiazole → HCID 59448375, compound

HRID 1925028Notes

Reaction equation

HRID 1925028 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[CH3:7][O:8][C:9]1[N:14]=[C:13]([O:15][CH3:16])[C:12](B(O)O)=[CH:11][N:10]=1.C([O-])(O)=O.[Na+]>COCCOC.O>[CH3:7][O:8][C:9]1[N:14]=[C:13]([O:15][CH3:16])[C:12]([C:2]2[S:3][CH:4]=[CH:5][N:6]=2)=[CH:11][N:10]=1

Participants

6

Reactant 3

HCID 764302-BromothiazoleHCID 516892Sodium BicarbonateHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acid

Product 1

HCID 59448375HCID 59448375, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

2-bromo-1,3-thiazole (commercially available from Aldrich, 0.165 ml, 1.829 mmol) was dissolved in degassed 1,2-Dimethoxyethane (DME) (5 ml). Pd(Ph3)4 (106 mg, 0.091 mmol) was added. The reaction mixture was stirred at room temperature for 15 min. [2,4-bis(methyloxy)-5-pyrimidinyl]boronic acid (commercially available from Aldrich, 707 mg, 3.84 mmol) and 5 mL of degassed 1M aqueous solution of NaHCO3 were added to the reaction mixture under N2 atmosphere. After 2 h 30 min stirring at 90° C., the reaction mixture was diluted with water and extracted with DCM. The collected organic phases were evaporated. The residue was purified by flash chromatography eluting with cyclohexane/EtOAc 5:1. 294 mg of the title compound were isolated as a yellow solid.

Workup

  1. additionwere added to the reaction mixture under N2 atmosphere
  2. extractionextracted with DCM
  3. customThe collected organic phases were evaporated
  4. customThe residue was purified by flash chromatography
  5. washeluting with cyclohexane/EtOAc 5:1

Sources & evidence

ORD record
ord-52b7ba7c53c74b49840acd4e066398c3
Source dataset
uspto-grants-2012_05
Patent number
US08178549B2

Reaction notes

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