Dimethylformamide → HCID 25260819, compound

HRID 1625201Notes

Reaction equation

HRID 1625201 reaction equation
Br[C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13](=[O:15])[NH2:14])[CH:8]=1)=[O:5].[F:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN(C=O)C>[Cu](I)I.O>[C:13]([C:9]1[CH:8]=[C:7]([NH:6][C:4](=[O:5])[C:3]2[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=2[O:27][C:24]2[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=2)[CH:12]=[CH:11][CH:10]=1)(=[O:15])[NH2:14]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 97324-FluorophenolHCID 62657Potassium Phosphate, TribasicHCID 17394186HCID 17394186, compound

Product 1

HCID 25260819HCID 25260819, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 962WaterSolvent

Procedure

To a mixture of 2-bromo-N-(3-carbamoylphenyl)benzamide (100 mg, 0.28 mmol), 4-fluorophenol (47.1 mg, 0.28 mmol), potassium phosphate (119 mg, 0.56 mmol), copper iodide (53 mg, 0.28 mmol) in a microwave vial was added 0.9 μL of DMF and 19 μL of water. The reaction was subjected to microwaves at 150° C. for 15 min. The reaction was cooled, the solids were filtered and the residue was purified by reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)) to give N-(3-carbamoylphenyl)-2-(4-fluorophenoxy)benzamide. LC/MS: m/z 351.0 (M+H)+ at 2.90 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationthe solids were filtered
  3. customthe residue was purified by reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA))

Sources & evidence

ORD record
ord-65562ef4ce6f46c390e4eed9c565fe19
Source dataset
uspto-grants-2014_07
Patent number
US08779197B2

Reaction notes

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