HCID 66877929, compound → HCID 58614814, compound

HRID 922873Notes

Reaction equation

HRID 922873 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[C:5]([NH:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10]([O:16][CH3:17])[CH:9]=1)=[O:6].[Br-].[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[Zn+]>C(OCC)(=O)C>[Cl:21][C:20]1[CH:19]=[CH:18][C:4]([C:5]([NH:7][C:8]2[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10]([O:16][CH3:17])[CH:9]=2)=[O:6])=[CH:3][C:2]=1[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=1

Participants

4

Reactant 2

HCID 66877929HCID 66877929, compoundHCID 178418723HCID 178418723, compound

Product 1

HCID 58614814HCID 58614814, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
155 °C

Procedure

3-bromo-4-chloro-N-(3,5-dimethoxyphenyl)benzamide was dissolved in 0.5 M 2-pyridylzincbromide (2.5 mL) and treated with Pd(PPh)3)4 (20 mg, 0.02 mmol). The reaction mixture was heated to 155° C. in a sealed tube for 20 min. in a microwave reactor. The resultant solution was diluted with Ethyl acetate and washed with 0.1 N sodium hydroxide and then brine. The organic layer was dried (MgSO4) and concentrated, and the crude residue was partially purified by silica gel chromatography. Pure 4-chloro-N-(3,5-dimethoxyphenyl)-3-(pyridin-2-yl)benzamide was obtained by a second purification on reverse phase HPLC. MS (Q1) 369.1 (M)+.

Workup

  1. washwashed with 0.1 N sodium hydroxide
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customthe crude residue was partially purified by silica gel chromatography

Sources & evidence

ORD record
ord-bc7f7f7f75144b77a66d334294e7c997
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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