HCID 121261628, compound → HCID 121261625, compound

HRID 530434Notes

Reaction equation

HRID 530434 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[CH:12]=[C:11]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[NH:21][C:22]([NH2:24])=[O:23])[S:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>C(#N)C.C(OCC)(=O)C.CC#N.CC#N.Cl[Pd]Cl>[NH2:24][C:22]([N:21]1[C:16]2[C:15](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[C:13]1[C:11]1[S:10][CH:9]=[C:8]([NH:7][C:6](=[O:25])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH:12]=1)=[O:23]

Participants

5

Reactant 1

HCID 121261628HCID 121261628, compound

Product 1

HCID 121261625HCID 121261625, compound

Reagents, catalysts & solvents 3

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a degassed solution of tert-butyl[5-({2-[(aminocarbonyl)amino]phenyl}ethynyl)-3-thienyl]carbamate (112 mg, 0.314 mmol, 1 eq) in anhydrous acetonitrile (2 mL) was added bis(acetonitrile)dichloropalladium(II) (16.3 mg, 0.2 eq). After the reaction mixture was heated at 90° C. for 50 minutes, it was cooled to room temp, and diluted with ethyl acetate. The mixture was washed with aqueous ammonium chloride, water, and brine, and lastly dried with anhydrous sodium sulfate. The upper solution was decanted, concentrated, and the dark brown mixture was subject to a gradient column chromatography (EtOAc-hex from 1; 100 to 1:5) to yield tert-butyl {5-[1-(aminocarbonyl)-1H-indol-2-yl]-3-thienyl}carbamate as white powder in amount of 23 mg.

Workup

  1. temperatureit was cooled to room temp
  2. washThe mixture was washed with aqueous ammonium chloride, water, and brine
  3. dry with materiallastly dried with anhydrous sodium sulfate
  4. customThe upper solution was decanted
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2fc2ca6bbb9249f9bb7dc1227b34662a
Source dataset
uspto-grants-2016_05
Patent number
US09353093B2

Reaction notes

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