Water → HCID 58437363, compound

HRID 881620Notes

Reaction equation

HRID 881620 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[C:9]([F:12])[CH:10]=2)[NH:5][CH:4]=1)#[N:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:20]([O:22][C:23](=[O:35])[C:24]1[CH:29]=[CH:28][C:27](F)=[CH:26][C:25]=1[O:31][CH2:32][O:33][CH3:34])[CH3:21].O>CN(C)C=O>[CH2:20]([O:22][C:23](=[O:35])[C:24]1[CH:29]=[CH:28][C:27]([N:5]2[C:6]3[C:11](=[CH:10][C:9]([F:12])=[C:8]([F:13])[CH:7]=3)[C:3]([C:1]#[N:2])=[CH:4]2)=[CH:26][C:25]=1[O:31][CH2:32][O:33][CH3:34])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 58437420HCID 58437420, compoundHCID 59224848HCID 59224848, compound

Product 1

HCID 58437363HCID 58437363, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 3-cyano-5,6-difluoroindole (0.25 g) in N,N-dimethylformamide (10 mL) were added cesium carbonate (0.91 g), 4-fluoro-2-methoxymethoxybenzoic acid ethyl ester (0.32 g), and this mixture was stirred at 75° C. overnight. This reaction mixture was poured into water, and this resulting mixture was extracted with ethyl acetate. This organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=10/90-75/25) to give the title compound (0.12 g).

Workup

  1. extractionthis resulting mixture was extracted with ethyl acetate
  2. washThis organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=10/90-75/25)

Sources & evidence

ORD record
ord-95533a93238b45dfa7059d61dd94f4dc
Source dataset
uspto-grants-2015_03
Patent number
US08993616B2

Reaction notes

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