HCID 66834104, compound → 2-[1-(6-Cyano-1-methanesulfonyl-1H-indol-2-yl)-1-methylethyl]-4-methoxy-benzoic acid methyl ester

HRID 2275062Notes

Reaction equation

HRID 2275062 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[C:12]([CH3:16])([CH3:15])[C:13]#[CH:14].Br[C:19]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][C:20]=1[NH:27][S:28]([CH3:31])(=[O:30])=[O:29]>[Cu](I)I.CN(C=O)C>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[C:12]([C:13]1[N:27]([S:28]([CH3:31])(=[O:30])=[O:29])[C:20]2[C:19]([CH:14]=1)=[CH:24][CH:23]=[C:22]([C:25]#[N:26])[CH:21]=2)([CH3:15])[CH3:16]

Participants

5

Reactant 2

HCID 66834104HCID 66834104, compoundHCID 866638152-(1,1-Dimethylprop-2-ynyl)-4-methoxy-benzoic acid methyl ester

Product 1

HCID 668342822-[1-(6-Cyano-1-methanesulfonyl-1H-indol-2-yl)-1-methylethyl]-4-methoxy-benzoic acid methyl esterYield 62%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To the DMF (2 ml) solution of 2-(1,1-dimethylprop-2-ynyl)-4-methoxy-benzoic acid methyl ester (Compound AA3, 134 mg, 0.577 mmol) and N-(2-bromo-5-cyanophenyl)methanesulfonamide (Compound AA5, 167 mg, 1.05 eq.), copper iodide (9 mg, 0.08 eq.) and TEA (129 μl, 1.6 eq.) were added, degassed and flushed with nitrogen gas, added with dichlorobis(triphenylphosphine) palladium (20 mg, 0.05 eq.), and then degassed and flushed again with nitrogen gas. After stirring for 2 hr at 90° C., the reaction solution was added with water, extracted with ethyl acetate. The organic layer was washed with an brine and dried over magnesium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (white solid, 152 mg, 62%).

Workup

  1. customdegassed
  2. customflushed with nitrogen gas
  3. customdegassed
  4. customflushed again with nitrogen gas
  5. additionthe reaction solution was added with water
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with an brine
  8. dry with materialdried over magnesium sulfate
  9. customThe drying agent was removed by filtration
  10. customthe residues obtained
  11. concentrationafter concentration under reduced pressure
  12. customwere purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-40d70ae733db4a5db4294d8709880f77
Source dataset
uspto-grants-2015_09
Patent number
US09126931B2

Reaction notes

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