Water → HCID 10904968, compound

HRID 277932Notes

Reaction equation

HRID 277932 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][N:9]2[C:22]=1I)=[O:4].[OH-].[K+].O.[CH3:29][S:30]SC>N1C=CC=CC=1.[Cu]>[F:1][C:2]([F:25])([F:24])[C:3]([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][N:9]2[C:22]=1[S:30][CH3:29])=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 12232Dimethyl DisulfideHCID 14797Potassium HydroxideHCID 11134296HCID 11134296, compound

Product 1

HCID 10904968HCID 10904968, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1049PyridineSolvent

Conditions

Temperature
104 °C

Procedure

The 2-trifluoroacetamido-3-iodo-6-benzoyl-imidazo[1,2-a]pyridine (1.00 g, 2.17 mmol) was dissolved in 20 ml of pyridine (predried over KOH and then molecular sieve 3A , 0.04% H2O) under argon atmosphere. Copper bronze (207 mg, 3.25 mmol) was added. To the golden suspension in brown solution was added methyldisulfide (160 μl, 2.17 mmol) via syringe. The reaction mixture was heated for 1 hour at 104° C. then 68 hours at 100° C. The evolution of the reaction was followed by NMR (in each case, a sample was taken, hydrolized and washed with ammonia/NH4Cl (1:9) before checking by NMR). When the reaction was complete, the reaction mixture was diluted in 3 L of EtOAc and stirred for 15 minutes. Two liters of NH4OH/NH4Cl 1:9 were added and the mixture was strongly stirred for 30 minutes in a 10 L funnel. The layers were separated and 2 L of NH4OH/NH4Cl (1:9) were added to the organic layer. The mixture was again stirred for 30 minutes and then left without stirring for 5 to 10 minutes. The layers were separated and the organic layer was washed with brine. The organic layers were removed in vacuo and the resulting brown solid was subjected to a vary rapid column chromatography (MeOH/CH2Cl2, 2:98) to give 670 mg (81%) of a yellow solid. NMR

Workup

  1. custom68 hours
  2. customat 100° C
  3. washhydrolized and washed with ammonia/NH4Cl (1:9)
  4. additionthe reaction mixture was diluted in 3 L of EtOAc
  5. additionTwo liters of NH4OH/NH4Cl 1:9 were added
  6. stirringthe mixture was strongly stirred for 30 minutes in a 10 L funnel
  7. customThe layers were separated
  8. addition2 L of NH4OH/NH4Cl (1:9) were added to the organic layer
  9. stirringThe mixture was again stirred for 30 minutes
  10. waitleft
  11. stirringwithout stirring for 5 to 10 minutes
  12. customThe layers were separated
  13. washthe organic layer was washed with brine
  14. customThe organic layers were removed in vacuo

Sources & evidence

ORD record
ord-dbca822148a344c09630a786eb669926
Source dataset
uspto-grants-2002_03
Patent number
US06358971B1

Reaction notes

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