Toluene → 2-Isopropyl-phenanthridin-6-ylamine

HRID 338188Notes

Reaction equation

HRID 338188 reaction equation
B1([C:7]2[C:12]([C:13]#[N:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)OCCCO1.Br[C:16]1[CH:22]=[C:21]([CH:23]([CH3:25])[CH3:24])[CH:20]=[CH:19][C:17]=1[NH2:18].C(=O)([O-])[O-].[K+].[K+].C1(C)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.C(O)C>[CH:23]([C:21]1[CH:20]=[CH:19][C:17]2[C:16](=[C:7]3[C:12](=[C:13]([NH2:14])[N:18]=2)[CH:11]=[CH:10][CH:9]=[CH:8]3)[CH:22]=1)([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 5213372-Bromo-4-isopropylanilineHCID 35296022-(1,3,2-Dioxaborinan-2-yl)benzonitrile

Product 1

HCID 668137132-Isopropyl-phenanthridin-6-ylamine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

A 500 ml round bottom flask was charged with 12.2 grams (65.4 mmol) of 2-cyanophenylboronic acid propanediol ester, 14.0 g (65.4 mmol) of 2-bromo-4-isopropylaniline, 2.27 (2 mmol) tetrakis(triphenylphosphine)palladium, 18.0 g (131 mmol) of potassium carbonate, 150 ml toluene, and 50 ml ethanol. The reaction was heated to reflux under N2 for 18 hours. After cooling to room temperature the reaction was extracted with ethyl acetate and water. The organic was washed with brine and then dried with magnesium sulfate. The solids were collected by filtration and the solvent removed from filtrate. The product was purified by silica gel chromatography using 94.5% dichloromethane, 5% methanol, 0.5% ammonium hydroxide as the eluent. The fractions containing the desired product were combined and the solvent removed. The product was confirmed by NMR and mass spectroscopy.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux under N2 for 18 hours
  3. extractionwas extracted with ethyl acetate and water
  4. washThe organic was washed with brine
  5. dry with materialdried with magnesium sulfate
  6. filtrationThe solids were collected by filtration
  7. customthe solvent removed from filtrate
  8. customThe product was purified by silica gel chromatography
  9. additionThe fractions containing the desired product
  10. customthe solvent removed

Sources & evidence

ORD record
ord-66f2ba15898f4dacbb517b1dece45724
Source dataset
uspto-grants-2014_11
Patent number
US08889864B2

Reaction notes

Loading…