Water → 8-Bromo-3-(4-fluorophenyl)-imidazo[1,5-a]pyridine

HRID 1423012Notes

Reaction equation

HRID 1423012 reaction equation
[Br:1][C:2]1[C:3]([CH2:8][NH:9][C:10](=O)[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.O.C(=O)([O-])[O-].[K+].[K+]>O=P(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]2[N:4]([C:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)=[N:9][CH:8]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 67194294N-(3-bromopyridin-2-ylmethyl)-4-fluoro-benzamide

Product 1

HCID 671955508-Bromo-3-(4-fluorophenyl)-imidazo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture of N-(3-bromopyridin-2-ylmethyl)-4-fluoro-benzamide (594 mg, 1.92 mmol) in POCl3 (5.0 mL) is warmed at reflux. After 1.5 hours, the mixture is cooled to room temperature and poured into water while adding crushed ice to control the exotherm. The mixture is made basic with potassium carbonate and the precipitate is collected by filtration to afford 8-bromo-3-(4-fluorophenyl)-imidazo[1,5-a]pyridine.

Workup

  1. temperatureis warmed
  2. temperatureat reflux
  3. additionwhile adding
  4. customcrushed ice
  5. filtrationthe precipitate is collected by filtration

Sources & evidence

ORD record
ord-8eca7b9c1663474aa8ed7425d631c30f
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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