Magnesium → 8-[4-(1,1-Dimethoxyethyl)phenyl]-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-8-ol

HRID 2383244Notes

Reaction equation

HRID 2383244 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:12][CH3:13])([O:10][CH3:11])[CH3:9])=[CH:4][CH:3]=1.[Mg].[CH:15]1[N:16]=[CH:17][N:18]2[CH2:23][CH2:22][CH2:21][C:20](=[O:24])[C:19]=12>O1CCCC1>[CH3:11][O:10][C:8]([C:5]1[CH:6]=[CH:7][C:2]([C:20]2([OH:24])[CH2:21][CH2:22][CH2:23][N:18]3[CH:17]=[N:16][CH:15]=[C:19]23)=[CH:3][CH:4]=1)([O:12][CH3:13])[CH3:9]

Participants

5

Reactant 3

HCID 5462224MagnesiumHCID 109117821-Bromo-4-(1,1-dimethoxyethyl)benzeneHCID 167520695H,6H,7H,8H-imidazo(1,5-a)pyridin-8-one

Product 1

HCID 669338218-[4-(1,1-Dimethoxyethyl)phenyl]-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-8-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The Grignard reagent, prepared from 3.68 mmol of 1-bromo-4-(1,1-dimethoxyethyl)benzene [53578-00-0] and 14.72 mmol of magnesium in 5.5 ml of tetrahydrofuran is added slowly dropwise to a solution of 1.84 mmol of 6,7-dihydro-5H-imidazo[1,5-a]pyridin-8-one [426219-51-4] in 10 ml of tetrahydrofuran under argon. The reaction mixture is stirred at room temperature for 12 hours and then quenched with 0.5N HCl. It is extracted with dichloromethane and the phases are separated. The aqueous phase is rendered basic with sodium hydrogen carbonate and the precipitated solid is isolated by filtration and dried at 40° C. The title compound is obtained as a greyish solid. Rt=3.42 (Gradient I). By the process described in Example 3 the following compounds are prepared analogously:

Workup

  1. customquenched with 0.5N HCl
  2. extractionIt is extracted with dichloromethane
  3. customthe phases are separated
  4. customthe precipitated solid is isolated by filtration
  5. customdried at 40° C

Sources & evidence

ORD record
ord-6c27cc338d0c4f17bcf95b976c4d32c5
Source dataset
uspto-grants-2012_09
Patent number
US08263615B2

Reaction notes

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