Potassium Carbonate → 3,5-Dimethyl-6-phenanthridinamine

HRID 1618461Notes

Reaction equation

HRID 1618461 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B1OC(C)(C)C(C)(C)O1)#[N:2].BrC1C=C(C)C=C(C)[C:20]=1[NH2:21].C(=O)([O-])[O-].[K+].[K+].[C:34]1([CH3:40])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.CO>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>[CH3:40][C:34]1[CH:39]=[CH:38][C:37]2[C:4]3[C:3]([CH:1]([NH2:2])[N:21]([CH3:20])[C:36]=2[CH:35]=1)=[CH:8][CH:7]=[CH:6][CH:5]=3

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 1705792-Bromo-4,6-dimethylanilineHCID 35702292-(2-Cyanophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 21867641Toluene methanol

Product 1

HCID 574535493,5-Dimethyl-6-phenanthridinamineYield 82%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Added together 2-cyanophenylboronic acid pinacol ester (13.7 g, 60 mmol), 2-bromo-4,6-dimethylaniline (10.0 g, 50 mmol), tetrakis(triphenylphosphine)palladium(0) (2.3 g, 2.0 mmol) and potassium carbonate (18.6 g, 138.21 mol) to a 125 mL of a 95/5 mixture of toluene/methanol. The solvents were degassed and the reaction mixture heated to reflux for 48 hours. After cooling, the reaction mixture was vacuum filtered and the organics evaporated and crude product was purified using silica gel column chromatography treated with triethylamine and 1:9 ethyl acetate and methylene chloride mixture as the eluants. The pure product was collected and concentrated to give 3,5-dimethyl-6-phenanthridinamine (9.1 g, 82% Yield).

Workup

  1. customThe solvents were degassed
  2. temperaturethe reaction mixture heated
  3. temperatureto reflux for 48 hours
  4. temperatureAfter cooling
  5. filtrationfiltered
  6. customthe organics evaporated
  7. customcrude product was purified
  8. additiontreated with triethylamine and 1:9 ethyl acetate and methylene chloride mixture as the eluants
  9. customThe pure product was collected
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-569ebac52b00458b9ef030d7965ed1b4
Source dataset
uspto-grants-2014_07
Patent number
US08766529B2

Reaction notes

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