Cesium carbonate → 3-(benzyloxy)-5-(biphenyl-3-yl)-6-(1-hydroxy-2-phenylethyl)-1-methylpyridin-2(1H)-one

HRID 625971Notes

Reaction equation

HRID 625971 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:26])[N:11]([CH3:25])[C:12]([CH:16]([OH:24])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:13](Br)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:32]=[CH:31][CH:30]=[C:29](B(O)O)[CH:28]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH2:1]([O:8][C:9]1[C:10](=[O:26])[N:11]([CH3:25])[C:12]([CH:16]([OH:24])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:13]([C:38]2[CH:37]=[C:36]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:41]=[CH:40][CH:39]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2734315(3-Phenylphenyl)boronic acidHCID 674201833-(benzyloxy)-5-bromo-6-(1-hydroxy-2-phenylethyl)-1-methylpyridin-2(1H)-one

Product 1

HCID 711499563-(benzyloxy)-5-(biphenyl-3-yl)-6-(1-hydroxy-2-phenylethyl)-1-methylpyridin-2(1H)-oneYield 25%

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Procedure

To a solution of 3-(benzyloxy)-5-bromo-6-(1-hydroxy-2-phenylethyl)-1-methylpyridin-2(1H)-one (0.34 g, 0.821 mmol) in 2 mL THY was added PdCl2(dppf)-CH2Cl2 adduct (67 mg, 0.082 mmol), biphenyl-3-ylboronic acid (179 mg, 0.903 mmol), and 1 N aqueous cesium carbonate solution (2 mL, 2 mmol). The resulting mixture was microwaved in a sealed vial at 155° C. for 10 min. The aqueous layer was removed and discarded, and the organic layer was collected, dried over anhydrous magnesium sulfate, concentrated and purified by silica gel chromatography to afford 3-(benzyloxy)-5-(biphenyl-3-yl)-6-(1-hydroxy-2-phenylethyl)-1-methylpyridin-2(1H)-one (100 mg, 0.205 mmol, 25% yield).

Workup

  1. customThe resulting mixture was microwaved in a sealed vial at 155° C. for 10 min
  2. customThe aqueous layer was removed
  3. customthe organic layer was collected
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-f3a24909980e4b99a960f6b4c3cc57e5
Source dataset
uspto-grants-2016_04
Patent number
US09309199B2

Reaction notes

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