Ammonium Chloride → 2-Bromo-7-(pyridin-3-yl)hydroxymethylimidazo[5,1-b]thiazole

HRID 230034Notes

Reaction equation

HRID 230034 reaction equation
C([Mg][Br:4])C.I[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.Br[C:13]1[S:17][C:16]2=[C:18]([CH:21]=[O:22])N=[CH:20][N:15]2[CH:14]=1.[Cl-].[NH4+:24]>O1CCCC1>[Br:4][C:16]1[S:17][C:13]2=[C:14]([C:6]3[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=3)[N:15]=[CH:20][N:24]2[C:18]=1[CH2:21][OH:22]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 707143-IodopyridineHCID 115287442-Bromoimidazo[5,1-b]thiazole-7-carbaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 230887952-Bromo-7-(pyridin-3-yl)hydroxymethylimidazo[5,1-b]thiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A 1 M tetrahydrofuran solution (0.9 ml) of ethylmagnesium bromide was added to a solution of 147 mg of 3-iodopyridine in 1 ml of tetrahydrofuran under an argon atmosphere, and the mixture was stirred at room temperature for 30 min. A solution of 149 mg of 2-bromo-7-formylimidazo[5,1-b]thiazole in 2 ml of tetrahydrofuran was added to the solution, and the mixture was stirred at that temperature for 2.5 hr. An aqueous saturated ammonium chloride solution was added to the reaction mixture to stop the reaction, and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine in that order and was then dried over magnesium sulfate. The solvent was removed by evaporation, and the residue was purified by column chromatography on silica gel (ethyl acetate:methanol=4:1) to give 147 mg of 2-bromo-7-(pyridin-3-yl)hydroxymethylimidazo[5,1-b]thiazole.

Workup

  1. stirringthe mixture was stirred at that temperature for 2.5 hr
  2. customthe reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine in that order
  5. dry with materialwas then dried over magnesium sulfate
  6. customThe solvent was removed by evaporation
  7. customthe residue was purified by column chromatography on silica gel (ethyl acetate:methanol=4:1)

Sources & evidence

ORD record
ord-255fcc0aefa748c88a0f4baca515730b
Source dataset
uspto-grants-2009_07
Patent number
US07563901B2

Reaction notes

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