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

HRID 17536
Notes
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Reaction equation

HRID 17536 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6093782
Bis(acetonitrile)dichloropalladium
Catalyst
HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-0ca3847f243b437983c3d219f6ea998b
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737166B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes