Methanol → 5-(3-methoxybenzyl)-1-(4-chlorobenzyl)pyridin-2(1H)-one

HRID 1948205Notes

Reaction equation

HRID 1948205 reaction equation
C([SiH](CC)CC)C.[Cl:8][C:9]1[CH:32]=[CH:31][C:12]([CH2:13][N:14]2[CH:19]=[C:18]([CH:20](O)[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=3)[CH:17]=[CH:16][C:15]2=[O:30])=[CH:11][CH:10]=1.CO>C(O)(C(F)(F)F)=O>[CH3:28][O:27][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[CH2:20][C:18]1[CH:17]=[CH:16][C:15](=[O:30])[N:14]([CH2:13][C:12]2[CH:11]=[CH:10][C:9]([Cl:8])=[CH:32][CH:31]=2)[CH:19]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 12052TriethylsilaneHCID 589669561-(4-chlorobenzyl)-5-(hydroxy(3-methoxyphenyl)methyl)pyridin-2(1H)-one

Product 1

HCID 589669395-(3-methoxybenzyl)-1-(4-chlorobenzyl)pyridin-2(1H)-oneYield 71.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

According to Scheme 7 Method D: Triethylsilane (3 eq, 0.84 mmol, 0.10 g) was added to a solution of 1-(4-chlorobenzyl)-5-(hydroxy(3-methoxyphenyl)methyl)pyridin-2(1H)-one (1 eq, 0.28 mmol, 0.10 g, Example 41) in TFA (2 mL). The mixture was stirred 1 hour at room temperature. Upon completion, MeOH was added and the solution was evaporated. The crude residue was partitioned between water and CH2Cl2. The aqueous layer was extracted with CH2Cl2. The combined organic layers were successively washed with brine, dried over MgSO4 and concentrated under vacuum to afford the crude product. Purification by flash chromatography (AIT Flashsmart prepacked column 10 g SiO2) (CH2Cl2/AcOEt 95/5 to 90/10) of the crude product afford the title compound 5-(3-methoxybenzyl)-1-(4-chlorobenzyl)pyridin-2(1H)-one (0.20 mmol, 0.07 g, 71%) as a yellow oil.

Workup

  1. customthe solution was evaporated
  2. customThe crude residue was partitioned between water and CH2Cl2
  3. extractionThe aqueous layer was extracted with CH2Cl2
  4. washThe combined organic layers were successively washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under vacuum
  7. customto afford the crude product
  8. customPurification by flash chromatography (AIT Flashsmart prepacked column 10 g SiO2) (CH2Cl2/AcOEt 95/5 to 90/10) of the crude product

Sources & evidence

ORD record
ord-a004048ab2f54766a91fbf529849293d
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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