Acetic Acid → HCID 67405781, compound

HRID 1056909Notes

Reaction equation

HRID 1056909 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:15])[CH:5]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)O[CH:8]=1.CC(O)=O.[NH2:20][C:21]1[CH:22]=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:25][CH:26]=1>O>[C:23]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:24]=[CH:25][CH:26]=[C:21]([N:20]2[CH:8]=[C:3]([O:2][CH3:1])[C:4](=[O:15])[CH:5]=[C:6]2[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:22]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 167173-AminobiphenylHCID 77230947HCID 77230947, compound

Product 1

HCID 67405781HCID 67405781, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 5-methoxy-2-phenyl-4H-pyran-4-one (35 mg, 0.17 mmol) in a 1:1 mixture of AcOH:water (0.6 mL) was added 3-aminobiphenyl (59 mg, 0.35 mmol). The reaction vessel was sealed and heated at 130° C. for 3 h before being cooled to room temperature and purified by reversed phase HPLC (2 cm×5 cm CI 8, acetonitrile-water gradient, 0.05% TFA added) to provide (44%) 1-(biphenyl-3-yl)-5-methoxy-2-phenylpyridin-4(1H)-one. LC/MS (M+H)+ 354.

Workup

  1. customThe reaction vessel was sealed
  2. temperaturebefore being cooled to room temperature
  3. custompurified by reversed phase HPLC (2 cm×5 cm CI 8, acetonitrile-water gradient, 0.05% TFA added)

Sources & evidence

ORD record
ord-b00ea238175649aa953ea6a0c3241ccf
Source dataset
uspto-grants-2016_07
Patent number
US09399651B2

Reaction notes

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