Potassium Carbonate → HCID 86689311, compound

HRID 1852495Notes

Reaction equation

HRID 1852495 reaction equation
O([C:9]1[C:10]([N+:18]([O-:20])=[O:19])=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH2:14][CH2:13][CH2:12]2)S(C(F)(F)F)(=O)=O.[NH2:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[C:25]#[N:26].C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[N+:18]([C:10]1[C:9]([NH:21][C:22]2[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=2)[C:25]#[N:26])=[CH:17][CH:16]=[C:15]2[C:11]=1[CH2:12][CH2:13][CH2:14]2)([O-:20])=[O:19]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 167023-AminobenzonitrileHCID 86689309HCID 86689309, compound

Product 1

HCID 86689311HCID 86689311, compoundYield 30.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A dry toluene (50 mL) suspension of 4-nitroindan-5-yl triflate (3.11 g, 10.0 mmol), 3-aminobenzonitrile (1.77 g, 15.0 mmol), potassium carbonate (1.38 g, 10.0 mmol), tetrakis(triphenylphosphine)palladium (0.57 g, 0.50 mmol), and triphenylphosphine (0.26 g, 1.00 mmol) was refluxed for 66 hours. After cooling on standing, insoluble was removed by filtration. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/5) to give the titled compound as orange crystal (0.84 g, yield 30%).

Workup

  1. temperaturewas refluxed for 66 hours
  2. temperatureAfter cooling
  3. custominsoluble was removed by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/5)

Sources & evidence

ORD record
ord-d10a85dd498e4f3c934cc3eefdf6c785
Source dataset
uspto-grants-2015_02
Patent number
US08962613B2

Reaction notes

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