Methyl iodide → 4-Benzyloxy-6-chloro-3-methyl-imidazo[4,5-c]pyridine

HRID 2208999Notes

Reaction equation

HRID 2208999 reaction equation
[CH2:1]([O:8][C:9]1[C:14]2[NH:15][CH:16]=[N:17][C:13]=2[CH:12]=[C:11]([Cl:18])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:14]2[N:15]([CH3:19])[CH:16]=[N:17][C:13]=2[CH:12]=[C:11]([Cl:18])[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178477827HCID 178477827, compound

Product 1

HCID 208206864-Benzyloxy-6-chloro-3-methyl-imidazo[4,5-c]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(benzyloxy)-6-chloro-3H-imidazo[4,5-c]pyridine 2.24 (1.00 g, 3.85 mmol) and K2CO3 (1.06 g, 7.70 mmol) were suspended in DMF and iodomethane (0.312 mL. 5.01 mmol) was added dropwise. The reaction was stirred for 2 hours and judged to be complete by LC and TLC. The reaction was concentrated, diluted with NaHCO3 (30 mL) and EtOAc (50 mL), and the layers were separated. The aqueous layer was extracted with EtOAc (3×50 mL), dried, filtered, and concentrated under reduced pressure to afford a mixture of regioisomers. Purification via flash chromatography (2→5% THF in CH2Cl2) afforded 4-(benzyloxy)-6-chloro-3-methyl-3H-imidazo[4,5-c]pyridine 2.25 as the first eluting isomer.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with NaHCO3 (30 mL) and EtOAc (50 mL)
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with EtOAc (3×50 mL)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto afford
  9. additiona mixture of regioisomers
  10. customPurification via flash chromatography (2→5% THF in CH2Cl2)

Sources & evidence

ORD record
ord-3044e53b974942f6ac54a34537c854a8
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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