Methyl iodide → HCID 89996149, compound

HRID 1480870Notes

Reaction equation

HRID 1480870 reaction equation
IC.[CH3:3][O:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([C:14]2[CH:18]=[N:17][NH:16][N:15]=2)[N:6]=1.[C:19](=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH3:3][O:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([C:14]2[CH:18]=[N:17][N:16]([CH3:19])[N:15]=2)[N:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 89996213HCID 89996213, compound

Product 1

HCID 89996149HCID 89996149, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Iodomethane (330 μL, 5.31 mmol) was added to a solution of 2-methoxy-3-nitro-6-(2H-1,2,3-triazol-4-yl)pyridine (Preparation 199, 235 mg, 1.063 mmol) and potassium carbonate (294 mg, 2.125 mmol) in THF (5.1 mL). The reaction mixture was stirred at room temperature for 72 hours. The solid was filtered and the filtrate concentrated in vacuo. The residue was purified using Biotage silica gel column chromatography eluting with cyclohexane/EtOAc 80/20 to 40/60 to afford the title compound as a beige solid (48 mg, 19%).

Workup

  1. filtrationThe solid was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was purified
  4. washeluting with cyclohexane/EtOAc 80/20 to 40/60

Sources & evidence

ORD record
ord-3d7e73a9c1524038b848f78e581cf66c
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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