Hydrochloric Acid → 7-Bromo-1-(3-methoxypropenyl)imidazo[1,5-a]pyridine

HRID 252348Notes

Reaction equation

HRID 252348 reaction equation
[Br-].[CH3:2][O:3][CH2:4][CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[H-].[Na+].[Br:27][C:28]1[CH:33]=[CH:32][N:31]2[CH:34]=[N:35][C:36]([CH:37]=O)=[C:30]2[CH:29]=1.Cl>CN(C)C=O>[Br:27][C:28]1[CH:33]=[CH:32][N:31]2[CH:34]=[N:35][C:36]([CH:37]=[CH:5][CH2:4][O:3][CH3:2])=[C:30]2[CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 22377376(2-Methoxy-ethyl)-triphenyl-phosphonium, bromideHCID 838395707-Bromoimidazo[1,5-a]pyridine-1-carbaldehyde

Product 1

HCID 668888487-Bromo-1-(3-methoxypropenyl)imidazo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of 12.04 g of (2-methoxyethyl)triphenylphosphonium bromide [55894-16-1] in 50 ml of anhydrous N,N-dimethylformamide is admixed with 2.60 g of sodium hydride (60% dispersion). The reaction mixture is stirred at room temperature for 30 minutes and a solution of 6.75 g of 7-bromoimidazo[1,5-a]pyridine-1-carbaldehyde in 20 ml of N,N-dimethylformamide is added. The reaction mixture is subsequently stirred at 50° C. for 1 hour. The reaction mixture is cooled to room temperature and poured onto ice-water. The quenched mixture is acidified with 1M HCl and extracted with tert-butyl methyl ether (3×100 ml). The combined organic phases are washed with water (100 ml) and brine (100 ml), dried over sodium sulphate and concentrated by evaporation. The title compound is identified on the basis of the Rf value from the residue by means of flash chromatography (SiO2 60F).

Workup

  1. stirringThe reaction mixture is subsequently stirred at 50° C. for 1 hour
  2. temperatureThe reaction mixture is cooled to room temperature
  3. additionpoured onto ice-water
  4. extractionextracted with tert-butyl methyl ether (3×100 ml)
  5. washThe combined organic phases are washed with water (100 ml) and brine (100 ml)
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-150386dfa9b24d6296fe18b05c093250
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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