HCID 69349823, compound → 1-(4-chlorobenzyl)-5-(4-(2-hydroxypropan-2-yl)phenyl)pyridin-2(1H)-one

HRID 1948235Notes

Reaction equation

HRID 1948235 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[CH:15][CH:14]=3)[CH:10]=[CH:9][C:8]2=[O:22])=[CH:4][CH:3]=1.[CH3:25][Mg]Br>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([OH:21])([CH3:25])[CH3:20])=[CH:15][CH:14]=3)[CH:10]=[CH:9][C:8]2=[O:22])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 69349823HCID 69349823, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 589669181-(4-chlorobenzyl)-5-(4-(2-hydroxypropan-2-yl)phenyl)pyridin-2(1H)-oneYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-50 °C

Procedure

According to Scheme 20: To a solution of 1-(4-chlorobenzyl)-5-(4-acetylphenyl)pyridin-2(1H)-one (1 eq, 0.20 mmol, 80 mg) in THF (5 mL) at −50° C. was added a solution of methyl magnesium bromide (3M, 1.3 eq, 0.30 mmol, 0.04 g) and the reaction stirred at −50° C. for 1 hour. The reaction was quenched at −78° C. with saturated aqueous NH4Cl. The reaction was allowed to warm to room temperature and diluted with AcOEt and the organic phase extracted (×3). The combined organic fractions were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 25 g SiO2) using CH2Cl2/AcOEt 80/20 and was recrystallized from pentane/Et2O to afford 1-(4-chlorobenzyl)-5-(4-(2-hydroxypropan-2-yl)phenyl)pyridin-2(1H)-one (0.08 mmol, 30 mg, 36%) as a white solid.

Workup

  1. customThe reaction was quenched at −78° C. with saturated aqueous NH4Cl
  2. temperatureto warm to room temperature
  3. additiondiluted with AcOEt
  4. extractionthe organic phase extracted (×3)
  5. dry with materialThe combined organic fractions were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 25 g SiO2)
  9. customwas recrystallized from pentane/Et2O

Sources & evidence

ORD record
ord-dd6a5767ab544bbabfc0ce5a9622d64e
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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