Dichloromethane → HCID 86628440, compound

HRID 2426365Notes

Reaction equation

HRID 2426365 reaction equation
[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH2:15][O:16]CC)[N:10]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:6]=2[C:5]([CH3:19])=[C:4]([CH3:20])[N:3]=1.ClCCl.B(Br)(Br)Br>CO>[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH2:15][OH:16])[N:10]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:6]=2[C:5]([CH3:19])=[C:4]([CH3:20])[N:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 25180025HCID 25180025, compound

Product 1

HCID 86628440HCID 86628440, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A 500 mL round bottom flask was charged with 4-chloro-2-(ethoxymethyl)-1-isobutyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridine (10.0 g, 33.8 mmol) and dichloromethane (250 mL) under a nitrogen atmosphere. The solution was cooled to 0° C. and boron tribromide (101 mL of 1M in dichloromethane, 101 mmol) was added through an addition funnel over 30 minutes. The reaction mixture was allowed to warm to room temperature and was stirred over night. Methanol was added slowly until no more fizzing occurred, then the solvent was partially removed under reduced pressure. More methanol was added (100 mL) as well as 6N hydrochloric acid (100 mL) and the solution was heated at reflux for 1 hour. The reaction mixture was then allowed to cool to room temperature and stirred over night. The solvent was partially removed under reduced pressure until a solid precipitated, which was isolated by filtration and washed with water, then triturated with ethyl acetate and hexanes to give 6.15 g of (4-chloro-1-isobutyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-2-yl)methanol as an off-white solid.

Workup

  1. temperatureto warm to room temperature
  2. customthe solvent was partially removed under reduced pressure
  3. additionMore methanol was added (100 mL) as well as 6N hydrochloric acid (100 mL)
  4. temperaturethe solution was heated
  5. temperatureat reflux for 1 hour
  6. temperatureto cool to room temperature
  7. stirringstirred over night
  8. customThe solvent was partially removed under reduced pressure until a solid
  9. customprecipitated
  10. customwhich was isolated by filtration
  11. washwashed with water
  12. customtriturated with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-a53d2e49ad6546d6a189b608df333240
Source dataset
uspto-grants-2011_06
Patent number
US07968563B2

Reaction notes

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