Sodium Thiosulfate → 1H-Imidazo(4,5-c)pyridine

HRID 2208995Notes

Reaction equation

HRID 2208995 reaction equation
Cl[C:2]1[N:7]=[C:6](S(C)(=O)=O)[C:5]2[N:12](COCC[Si](C)(C)C)[CH:13]=[N:14][C:4]=2[CH:3]=1.[Cl:23][C:24]1[N:29]=[C:28]([S:30]([CH3:33])(=[O:32])=[O:31])[C:27]2[N:34]=[CH:35][N:36]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[C:26]=2[CH:25]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.[O-]S([O-])(=S)=O.[Na+].[Na+]>ClCCl.C(OCC)(=O)C>[N:14]1[C:4]2[CH:3]=[CH:2][N:7]=[CH:6][C:5]=2[NH:12][CH:13]=1.[Cl:23][C:24]1[N:29]=[C:28]([S:30]([CH3:33])(=[O:32])=[O:31])[C:27]2[N:34]=[CH:35][N:36]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[C:26]=2[CH:25]=1

Participants

8

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 1234746106-chloro-4-(methylsulfonyl)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-c]pyridineHCID 1237516726-chloro-4-(methylsulfonyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-c]pyridine

Product 2

HCID 92271H-Imidazo(4,5-c)pyridineHCID 1237516726-chloro-4-(methylsulfonyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-c]pyridine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Into a solution of 6-chloro-4-(methylsulfonyl)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-c]pyridine 2.07 and 6-chloro-4-(methylsulfonyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-c]pyridine 2.08 (536 mg, 1.62 mmol) in dichloromethane (10 mL) at 0° C., was added mCPBA (<77%, 841 mg) and mixture was warmed to room temperature. After 2 h, a 20% solution of Na2S2O3 (aq) (20 mL) was added and reaction mixture stirred at room temperature for 15 minutes. The mixture was taken up in ethyl acetate (150 mL) and washed with saturated NaHCO3 (aq) and brine. The combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure, This residue was purified by silica gel column chromatography (eluted with 30% to 100% of ethyl acetate in hexane) to yield 6-chloro-4-(methylsulfonyl)-34(2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-c]pyridine 2.09 and 6-chloro-4-(methylsulfonyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-c]pyridine 2.10.

Workup

  1. customreaction mixture
  2. washwashed with saturated NaHCO3 (aq) and brine
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThis residue was purified by silica gel column chromatography (eluted with 30% to 100% of ethyl acetate in hexane)

Sources & evidence

ORD record
ord-42668da1ca6f4f329f0dbc6b1c61f246
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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