Cesium carbonate → HCID 58541696, compound

HRID 600257Notes

Reaction equation

HRID 600257 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([CH:15]=2)[CH:13]=[CH:12][S:11]3)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:22]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:27]=CC=C[CH:23]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:27]2[CH:22]=[CH:23][N:14]=[C:10]([S:11][CH3:12])[N:9]=2)[CH:13]=[CH:12][S:11]3)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 8681986-(4-Fluorophenyl)imidazo[2,1-b][1,3]thiazole

Product 1

HCID 58541696HCID 58541696, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 6-(4-fluorophenyl)-imidazo[2,1-b]thiazole (J) (6.0 g, 27.6 mmol), 4-iodo-2-thiomethylpyrimidine (10.4 g, 41.3 mmol), cesium carbonate (13.4 g, 41.3 mmol), triphenylphosphine (2.88 g, 11 mmol), and palladium acetate (1.22 g, 5.5 mmol) is added anhydrous dimethylformamide (60 mL). The reaction mixture is sealed and shaken at 80° C. for 12 hours. The reaction was quenched by addition of water (200 mL). The aqueous layer is extracted with ethyl acetate (3×100 mL). The organic phase is washed sequentially with water (100 mL) and a saturated aqueous, sodium chloride solution (100 mL). The organic phase is dried over sodium sulfate, filtered, and the solvent evaporated in vacuo. The crude product is purified by silica gel column chromatography, eluting with a gradient of ethyl acetate/hexane (20-30%). After evaporation of the solvent, 6-(4-fluorophenyl)-5-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[2,1-b]thiazole (K) (Compound CXXXIX, Table 2) is obtained as a white solid (3.5 g, 37%) m.p. 151-152° C.;

Workup

  1. customThe reaction mixture is sealed
  2. customThe reaction was quenched by addition of water (200 mL)
  3. extractionThe aqueous layer is extracted with ethyl acetate (3×100 mL)
  4. washThe organic phase is washed sequentially with water (100 mL)
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo
  8. customThe crude product is purified by silica gel column chromatography
  9. washeluting with a gradient of ethyl acetate/hexane (20-30%)
  10. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-50ce19b79f934a8b8f52a6f55ac7f09f
Source dataset
uspto-grants-2011_03
Patent number
US07902192B2

Reaction notes

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