Water → HCID 70982101, compound

HRID 2175235Notes

Reaction equation

HRID 2175235 reaction equation
Br[C:2]1[S:3][C:4]([Br:7])=[CH:5][N:6]=1.[OH:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12]([O:14][CH3:15])=[O:13].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Br:7][C:4]1[S:3][C:2]([O:8][C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])=[N:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 88068Methyl 3-HydroxybenzoateHCID 3123942,5-Dibromothiazole

Product 1

HCID 70982101HCID 70982101, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2,5-dibromothiazole (500 mg, 2.06 mmol), methyl 3-hydroxybenzoate (313 mg, 2.06 mmol) and potassium carbonate (341 mg, 2.47 mmol) in DMF (4 mL) was heated at 140° C. in a microwave reactor for 20 min. After cooling to room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over anhydrous MgSO4, filtered, and concentrated. The resulting residue was purified by flash chromatography (0-100% ethyl acetate:hexanes) to afford the title compound (520 mg, 80% yield). LCMS, [M+H]+=315.9.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by flash chromatography (0-100% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-768c7b7ee1384ab4b48d0a95f4bb5e30
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

Loading…