Potassium Carbonate → HCID 25918949, compound

HRID 2368404Notes

Reaction equation

HRID 2368404 reaction equation
[Br:1]Br.[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([NH2:15])[S:13][CH:14]=2)=[CH:6][CH:5]=1.C([O-])([O-])=O.[K+].[K+]>C(O)(=O)C.O.CCOC(C)=O>[Br:1][C:14]1[S:13][C:12]([NH2:15])=[N:11][C:10]=1[C:7]1[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 24408BromineHCID 7223714-(4-fluorophenyl)-1,3-thiazol-2-amine

Product 1

HCID 25918949HCID 25918949, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Bromine was added to a solution of 4-(4-fluoro-phenyl)-thiazol-2-ylamine (12 g, 62 mmol) in acetic acid at room temperature. The mixture was stirred at room temperature for 30 sec and solidified. The mixture was diluted with water and poured to ice-water. The light grey suspension was filtered. The solid obtained was taken up in EtOAc and carefully basified with aqueous K2CO3 (pH was adjusted to 8˜9). The EtOAc extract was dried over MgSO4 and concentrated to give crude 5-bromo-4-(4-fluoro-phenyl)-thiazol-2-ylamine (15.15 g). This was then mixed with 4-fluorophenol (6.9 g, 62 mmol) and Cs2CO3 (22 g, 68 mmol) in acetonitrile (120 mL) and heated at 70° C. for 2 h and concentrated. The residue was partitioned between EtOAc and water. The organic extract was dried over MgSO4, concentrated and chromatographed to give the title compound with some impurities. m/z 305.1 (MH+).

Workup

  1. filtrationThe light grey suspension was filtered
  2. customThe solid obtained
  3. extractionThe EtOAc extract
  4. dry with materialwas dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b9a1feb843f3466a82ef5ddfd2cce25b
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

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