Benzyl Alcohol → HCID 178477827, compound

HRID 2208998Notes

Reaction equation

HRID 2208998 reaction equation
Cl[C:2]1[C:7]2[NH:8][CH:9]=[N:10][C:6]=2[CH:5]=[C:4]([Cl:11])[N:3]=1.[OH-].[Na+].[CH2:14]([OH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14]([O:21][C:2]1[C:7]2[NH:8][CH:9]=[N:10][C:6]=2[CH:5]=[C:4]([Cl:11])[N:3]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 244Benzyl AlcoholHCID 14798Sodium HydroxideHCID 178477826HCID 178477826, compound

Product 1

HCID 178477827HCID 178477827, compound

Conditions

Temperature
150 °C

Procedure

To a solution of 4,6-dichloro-3H-imidazo[4,5-c]pyridine (2.00 g, 10.6 mmol) in BnOH (23 mL) was added powdered NaOH (1.28 g, 31.9 mmol) and the reaction was heated to 150° C. overnight. The benzyl alcohol was removed by vacuum distillation, and the residue was suspended in water (15 mL) and AcOH (3 mL) was added to bring the pH to ˜7. The aqueous layer was extracted with CH2Cl2 (3×50 mL). The combined organics were dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (1:1 hex EtOAc-->EtOAc/10% MeOH) to afford 4-(benzyloxy)-6-chloro-3H-imidazo[4,5-c]pyridine 2.24.

Workup

  1. customThe benzyl alcohol was removed by vacuum distillation
  2. additionAcOH (3 mL) was added
  3. extractionThe aqueous layer was extracted with CH2Cl2 (3×50 mL)
  4. dry with materialThe combined organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (1:1 hex EtOAc-->EtOAc/10% MeOH)

Sources & evidence

ORD record
ord-36a824effd12405d80fba73d31855217
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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