Dichloromethane → HCID 22032228, compound

HRID 1792466Notes

Reaction equation

HRID 1792466 reaction equation
Cl[C:2]1C=CC=C(C(OO)=O)C=1.[Br:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([C:19]([C:22]3[O:23][C:24](SC)=[N:25][N:26]=3)=[CH:20][N:21]=2)[CH:18]=1.ClCCl.[S:32]([O-:36])([O-])(=[O:34])=S.[Na+].[Na+]>C(OCC)(=O)C>[Br:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([C:19]([C:22]3[O:23][C:24]([S:32]([CH3:2])(=[O:36])=[O:34])=[N:25][N:26]=3)=[CH:20][N:21]=2)[CH:18]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 22031037HCID 22031037, compound

Product 1

HCID 22032228HCID 22032228, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.16 g of m-chloroperbenzoic acid was added to a mixture of 981 mg 6-bromo-3-(5-methylsulfanyl[1,3,4]oxadiazol-2-yl)imidazo[1,2-a]pyridine (compound in Production Example 279) and 30 mL dichloromethane under ice-coolingd water, then retuned to room temperature and stirred overnight. Ethyl acetate and an aqueous saturated sodium thiosulfate solution were added to the reaction solution, and the mixture was stirred. The organic layer was separated, washed twice with an aqueous saturated sodium bicarbonate solution and then with brine and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was evaporated. 995 mg crude product of a mixture of 6-bromo-3-(5-methanesulfinyl[1,3,4]oxadiazol-2-yl)imidazo[1,2-a]pyridine and 6-bromo-3-(5-methylsulfonyl[1,3,4]oxadiazol-2-yl)imidazo[1,2-a]pyridine was obtained as pale brown crystals. A mixture of 150 mg of this mixture, 90 μL methylamine (30% methanol solution) and 10 mL methanol was stirred at room temperature for 10 minutes. Ethyl acetate, tetrahydrofuran and water were added to the reaction solution, and the organic layer was separated. The aqueous layer was saturated with common salt and then extracted with ethyl acetate. The combined organic layer was washed with brine and then dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was evaporated. The resulting residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 121 mg of the title compound as a white solid.

Workup

  1. customretuned to room temperature
  2. stirringthe mixture was stirred
  3. customThe organic layer was separated
  4. washwashed twice with an aqueous saturated sodium bicarbonate solution
  5. dry with materialwith brine and dried over anhydrous sodium sulfate
  6. filtrationThe drying agent was filtered off
  7. customthe filtrate was evaporated
  8. addition995 mg crude product of a mixture of 6-bromo-3-(5-methanesulfinyl[1,3,4]oxadiazol-2-yl)imidazo[1,2-a]pyridine

Sources & evidence

ORD record
ord-0797dd6832b142a3b1f415dd8aed0253
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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