Water → HCID 86637902, compound

HRID 2389330Notes

Reaction equation

HRID 2389330 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5](=[O:24])[N:6]([CH2:8][CH2:9][CH2:10][C:11]2[CH:12]=[C:13]([CH:21]=[CH:22][CH:23]=2)[O:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:7]=1.[C:25]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:26](B(O)O)=[CH:27][CH:28]=[CH:29][CH:30]=1.C([O-])([O-])=O.[Na+].[Na+].O>[Cl-].[Na+].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>[C:25]1([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=1[C:2]1[CH:3]=[CH:4][C:5](=[O:24])[N:6]([CH2:8][CH2:9][CH2:10][C:11]2[CH:12]=[C:13]([CH:21]=[CH:22][CH:23]=2)[O:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:7]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 4589187Biphenyl-2-boronic acidHCID 86637903HCID 86637903, compound

Product 1

HCID 86637902HCID 86637902, compoundYield 82.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 5234Sodium ChlorideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl {3-[3-(5-bromo-2-oxopyridin-1(2H)-yl) propyl]phenoxy}acetate (187.5 mg), 2-biphenylboronic acid (104 mg), Na2CO3(504 mg), Pd(PPh3)4 (27 mg), water (4 mL) and toluene (8 mL) were stirred under N2 gas atmosphere at 100° C. for 3 hours. The reaction mixture was cooled to ambient temperature, diluted with 5% aqueous sodium chloride solution and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=70:30-50:50). to give ethyl {3-[3-(5-biphenyl-2-yl-2-oxopyridin-1(2H)-yl)propyl]phenoxy}acetate (184 mg) as a colorless oil.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=70:30-50:50)

Sources & evidence

ORD record
ord-f0d87db745f74f12a6453e51f39f8149
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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