Carbon tetrabromide → HCID 22631725, compound

HRID 1840436Notes

Reaction equation

HRID 1840436 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)Br.[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31]O.C([S:36][C:37]1[N:38]=[CH:39][N:40]2[CH:44]=[CH:43][S:42][C:41]=12)(=O)C.C[O-].[Na+].CO.BrCC1C=CC=CN=1.[Cl-].[NH4+]>ClCCl.CO>[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31][S:36][C:37]1[N:38]=[CH:39][N:40]2[CH:44]=[CH:43][S:42][C:41]=12

Participants

10

Reactant 7

HCID 11205Carbon tetrabromideHCID 11474PiconolHCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 5642092-(Bromomethyl)pyridineHCID 226316637-Acetylthioimidazo[5,1-b]thiazoleHCID 23694274Sodium methanolate methanol

Product 1

HCID 22631725HCID 22631725, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

Triphenylphosphine (2.95 g) and 3.73 g of carbon tetrabromide were added to a solution of 0.724 ml of (pyridin-2-yl)methanol in 40 ml of dichloromethane under ice cooling, and the mixture was stirred at that temperature for 1.5 hr. The reaction solution was purified by column chromatography on silica gel (dichloromethane:methanol=30:1) to prepare 2-bromomethylpyridine. A solution of 990 mg of 7-acetylthioimidazo[5,1-b]thiazole in 5 ml of methanol was cooled in ice. A 1.018 M sodium methoxide/methanol solution (5.4 ml) was added to the cooled solution, and the mixture was stirred for 30 min. The above solution of 2-bromomethylpyridine in 5 ml of dichloromethane was added thereto, and the mixture was stirred at room temperature for 20 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate three times. The organic layer was washed with saturated brine, and was then dried over anhydrous magnesium sulfate. The solvent was removed by distillation, and the residue was purified by column chromatography on silica gel (dichloromethane:methanol=20:1) to prepare 776 mg of 7-(pyridin-2-yl)methylthioimidazo[5,1-b]thiazole.

Workup

  1. customThe reaction solution was purified by column chromatography on silica gel (dichloromethane:methanol=30:1)
  2. customto prepare 2-bromomethylpyridine
  3. stirringthe mixture was stirred for 30 min
  4. stirringthe mixture was stirred at room temperature for 20 hr
  5. extractionthe mixture was extracted with ethyl acetate three times
  6. washThe organic layer was washed with saturated brine
  7. dry with materialwas then dried over anhydrous magnesium sulfate
  8. customThe solvent was removed by distillation
  9. customthe residue was purified by column chromatography on silica gel (dichloromethane:methanol=20:1)
  10. customto prepare 776 mg of 7-(pyridin-2-yl)methylthioimidazo[5,1-b]thiazole

Sources & evidence

ORD record
ord-2574ec177cde42b99fc1ff0a10d6ffdf
Source dataset
uspto-grants-2004_01
Patent number
US06680313B2

Reaction notes

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