Cesium carbonate → 3-[(4-methoxybenzyl)oxy]-4'-phenyl-4H-1,2'-bipyridin-4-one

HRID 1056891Notes

Reaction equation

HRID 1056891 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][O:8][C:9]2[C:14](=[O:15])[CH:13]=[CH:12][N:11]([C:16]3[CH:21]=[C:20](B(O)O)[CH:19]=[CH:18][N:17]=3)[CH:10]=2)=[CH:5][CH:4]=1.I[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][O:8][C:9]2[C:14](=[O:15])[CH:13]=[CH:12][N:11]([C:16]3[CH:21]=[C:20]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:19]=[CH:18][N:17]=3)[CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 11575IodobenzeneHCID 67418584{3-[(4-methoxybenzyl)oxy]-4-oxo-4H-1,2'-bipyridin-4'-yl}boronic acid

Product 1

HCID 674046263-[(4-methoxybenzyl)oxy]-4'-phenyl-4H-1,2'-bipyridin-4-one

Conditions

Temperature
135 °C

Procedure

To a 20 mL microwave vial (Biotage) was added {3-[(4-methoxybenzyl)oxy]-4-oxo-4H-1,2′-bipyridin-4′-yl}boronic acid (300 mg, 0.85 mmol), iodobenzene (348 mg, 1.70 mmol), cesium carbonate (6 mL of a 1.0 M aq solution, 6.0 mmol), and 69.6 mg (0.085 mmol) I,Γ-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex. The vial was sealed and the reaction mixture was heated at 135° C. under microwave irradiation for 15 minutes, then cooled. The organic layer was separated, washed with 5 mL water, dried over Na2S04, filtered, and concentrated in vacuo. Purification by flash chromatography (silica gel, 0-10% MeOH in EtOAc gradient) afforded 3-[(4-methoxybenzyl)oxy]-4′-phenyl-4H-1,2′-bipyridin-4-one. LCMS (M+H)+=385.4.

Workup

  1. customThe vial was sealed
  2. temperaturecooled
  3. customThe organic layer was separated
  4. washwashed with 5 mL water
  5. customdried over Na2S04
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography (silica gel, 0-10% MeOH in EtOAc gradient)

Sources & evidence

ORD record
ord-c228d08c011449fdb712b4845f7f78b1
Source dataset
uspto-grants-2016_07
Patent number
US09399651B2

Reaction notes

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