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

HRID 61687Notes

Reaction equation

HRID 61687 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 AA3, 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 dicholorobis(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-a58d2fd7fa4f4359a8324c9c29e54fd3
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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