6-(4-Fluorophenyl)imidazo[2,1-b][1,3]thiazole → HCID 58541623, compound

HRID 600258Notes

Reaction equation

HRID 600258 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:21]=[CH:20][N:19]=[C:18](SC)[N:17]=2)[CH:13]=[CH:12][S:11]3)=[CH:4][CH:3]=1.F[C:25]1C=CC(C2N=C3N(C=2)C=CS3)=CC=1.O[O:40][S:41]([O-:43])=O.[K+]>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:21]=[CH:20][N:19]=[C:18]([S:41]([CH3:25])(=[O:43])=[O:40])[N:17]=2)[CH:13]=[CH:12][S:11]3)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8681986-(4-Fluorophenyl)imidazo[2,1-b][1,3]thiazoleHCID 23707502Potassium hydroxy sulfiteHCID 58541696HCID 58541696, compound

Product 1

HCID 58541623HCID 58541623, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of the mixture (1.1:1) of 6-(4-fluorophenyl)-5-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[2,1-b]thiazole (K) and 6-(4-fluorophenyl)-imidazo[2,1-b]thiazole (J) (0.205 g, 0.6 mmol) in methanol (25 mL) is added drop-wise a solution of oxone (1.23 g, 1.8 mmol) in water (5 mL). The reaction is stirred at room temperature for 16 hours. The volatiles are removed in vacuo at room temperature. To the residue is added dichloromethane. The organic phase is washed sequentially with water and a saturated, aqueous sodium chloride solution. The organic phase is dried over anhydrous sodium sulfate, filtered, and the solvent evaporated in vacuo. The crude product is purified by silica gel column chromatography, eluting with ethyl acetate hexane (1:1) to yield 6-(4-fluorophenyl)-5-(2-methanesulfonyl-pyrimidin-4-yl)-imidazo[2,1-b]thiazole (L) (Compound CXL, Table 2) as a white solid (0.113 g, 98%); m.p. 197-198° C.;

Workup

  1. customThe volatiles are removed in vacuo at room temperature
  2. additionTo the residue is added dichloromethane
  3. washThe organic phase is washed sequentially with water
  4. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo
  7. customThe crude product is purified by silica gel column chromatography
  8. washeluting with ethyl acetate hexane (1:1)

Sources & evidence

ORD record
ord-7aaf4a69822e4ba4bc95766f383be490
Source dataset
uspto-grants-2011_03
Patent number
US07902192B2

Reaction notes

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