N,N-Dimethylglycine → 5-Benzyloxy-2-(3-cyano-4-phenylpyrrole-1-yl)isonicotinic acid ethyl ester

HRID 570854Notes

Reaction equation

HRID 570854 reaction equation
[C:1]([C:3]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][NH:5][CH:4]=1)#[N:2].[CH2:14]([O:16][C:17](=[O:33])[C:18]1[C:23]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:22][N:21]=[C:20](Br)[CH:19]=1)[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)CC(O)=O>CS(C)=O.[Cu](I)I>[CH2:14]([O:16][C:17](=[O:33])[C:18]1[C:23]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:22][N:21]=[C:20]([N:5]2[CH:6]=[C:7]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:3]([C:1]#[N:2])=[CH:4]2)[CH:19]=1)[CH3:15]

Participants

7

Reactant 4

HCID 673N,N-DimethylglycineHCID 10796Cesium carbonateHCID 37214604-Phenyl-1H-pyrrole-3-carbonitrileHCID 866451665-Benzyloxy-2-bromoisonicotinic acid ethyl ester

Product 1

HCID 594778055-Benzyloxy-2-(3-cyano-4-phenylpyrrole-1-yl)isonicotinic acid ethyl esterYield 52.9%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 3-cyano-4-phenylpyrrole (0.20 g) in dimethylsulfoxide (2 mL) was added 5-benzyloxy-2-bromoisonicotinic acid ethyl ester (0.30 g), cesium carbonate (0.30 g), copper iodide (0.010 g) and N,N-dimethyl glycine (0.020 g) at room temperature, and this mixture was stirred at 110° C. for 8 hours. The insoluble material was removed by suction through a Celite pad. This filtrate was poured into water, and this mixture was extracted with ethyl acetate. This organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=10/90-60/40) to give the title compound (0.20 g).

Workup

  1. customThe insoluble material was removed by suction through a Celite pad
  2. additionThis filtrate was poured into water
  3. extractionthis mixture was extracted with ethyl acetate
  4. washThis organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=10/90-60/40)

Sources & evidence

ORD record
ord-053ad558c43148bf9b642fe2b18426b3
Source dataset
uspto-grants-2015_05
Patent number
US09023882B2

Reaction notes

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