Ethanol → (2R)-5-[4-(2-Hydroxy-4-pyridin-3-yl-butoxy)phenyl]-1-methyl-1H-pyridin-2-one

HRID 1856689Notes

Reaction equation

HRID 1856689 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+].[Si]([O:26][C@H:27]([CH2:39][CH2:40][C:41]1[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=1)[CH2:28][O:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)(C(C)(C)C)(C)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[OH:26][C@H:27]([CH2:39][CH2:40][C:41]1[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=1)[CH2:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([C:2]2[CH:3]=[CH:4][C:5](=[O:9])[N:6]([CH3:8])[CH:7]=2)=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 11200434(2R)-4-[2-(tert-butyldimethylsilanyloxy)-4-pyridin-3-yl-butoxy]benzeneboronic acidHCID 234243102(1H)-Pyridinone, 5-iodo-1-methyl-

Product 1

HCID 53655632(2R)-5-[4-(2-Hydroxy-4-pyridin-3-yl-butoxy)phenyl]-1-methyl-1H-pyridin-2-one

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to the method described in Example 7c) from 5-iodo-N-methylpyridin-2-one (Example 13a), 0.276 g), ethanol (4 ml), toluene (10 ml), 2M aqueous sodium carbonate (0.58 ml), (2R)-4-[2-(tert-butyldimethylsilanyloxy)-4-pyridin-3-yl-butoxy]benzeneboronic acid (Example 7b), 0.471 g), and tetrakis(triphenylphosphine)palladium(0) (0.03 g). After work up, the residue was purified by column chromatography over silica eluting dichloromethane:methanol (95:5) to give the title compound as a foam (0.191 g).

Workup

  1. customPrepared
  2. customAfter work up, the residue was purified by column chromatography over silica
  3. washeluting dichloromethane:methanol (95:5)

Sources & evidence

ORD record
ord-f934aa0d24504a50bce1a726070c685a
Source dataset
uspto-grants-2000_11
Patent number
US06143751

Reaction notes

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