Chloroform → 2-tert-butyl-4-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-phenyl-1H-indole-7-carbonitrile

HRID 17536

Reaktionsgleichung

Reaktionsgleichung von HRID 17536
[NH2:1][C:2]1[C:7]([C:8]#[C:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[C:6]([N:14]2[CH2:18][CH2:17][C@H:16]([N:19]([CH3:21])[CH3:20])[CH2:15]2)[C:5]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:4][C:3]=1[C:28]#[N:29].C(Cl)(Cl)Cl.C(=O)([O-])O.[Na+]>C(#N)C.CC#N.CC#N.Cl[Pd]Cl>[C:10]([C:9]1[NH:1][C:2]2[C:7]([CH:8]=1)=[C:6]([N:14]1[CH2:18][CH2:17][C@H:16]([N:19]([CH3:21])[CH3:20])[CH2:15]1)[C:5]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[CH:4][C:3]=2[C:28]#[N:29])([CH3:13])([CH3:11])[CH3:12]

Komponenten

6

Edukt 3

HCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 866308714-Amino-6-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-(3,3-dimethylbutyn-1-yl)biphenyl-3-carbonitrile

Produkt 1

HCID 685851312-tert-butyl-4-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-phenyl-1H-indole-7-carbonitrileAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6093782Bis(acetonitrile)dichloropalladiumKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

4-Amino-6-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-(3,3-dimethylbutyn-1-yl)biphenyl-3-carbonitrile (I-246) (54 mg, 0.14 mmol) was dissolved in acetonitrile (3 ml), and at room temperature, bis(acetonitrile)palladium(II) dichloride (7.3 mg, 0.28 mmol) was added, followed by heating under reflux for 3 hours. After cooling to room temperature, the reaction liquid was fractionated with chloroform and an aqueous saturated sodium hydrogencarbonate solution. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=95:5) to obtain a crude product of the entitled compound (32 mg, 60%) as a pale brown gel. This was recrystallized from hexane/diethyl ether to obtain the entitled compound (15 mg) as a pale brown powder.

Aufarbeitung

  1. temperatureby heating
  2. temperatureunder reflux for 3 hours
  3. customthe reaction liquid
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe insoluble matter was separated by filtration
  7. customthe solvent was evaporated away
  8. customthe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=95:5)

Quellen und Nachweise

ORD-Eintrag
ord-0ca3847f243b437983c3d219f6ea998b
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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