Toluene → HCID 70654352, compound

HRID 539492

Reaction equation

HRID 539492 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[C:4]#[N:5].CC1(C)C(C)(C)OB([C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[NH2:22])O1.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:2]2[C:3](=[C:4]([NH2:5])[N:22]=[C:21]3[C:20]=2[CH:26]=[CH:25][CH:24]=[CH:23]3)[CH:6]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 27346522-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 217840962-Bromo-5-methoxybenzonitrileHCID 22031701Potassium phosphate, tribasic, monohydrate

Product 1

HCID 70654352HCID 70654352, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

2-Bromo-5-methoxybenzonitrile (1.32 g, 6.23 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.36 g, 6.23 mmol), bis(triphenylphosphine)palladiumdichloride (0.437 g, 0.623 mmol) and potassium phosphate monohydrate (4.30 g, 18.68 mmol) were added to toluene (30 mL) and water (3 mL). The reaction mixture was degassed with bubbled nitrogen gas for 30 minutes before being refluxed under nitrogen for 15 h. After cooling, the reaction mixture was filtered through Celite® and the organic layer was extracted with ethyl acetate. After removal of the solvents, the crude material was triturated with 40 mL of DCM followed by 50 mL of hexanes to give 8-methoxyphenanthridin-6-amine (0.95 g, 68%) as a light yellow solid. The product was confirmed by GC/MS and NMR.

Workup

  1. customThe reaction mixture was degassed with bubbled nitrogen gas for 30 minutes
  2. temperaturebefore being refluxed under nitrogen for 15 h
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered through Celite®
  5. extractionthe organic layer was extracted with ethyl acetate
  6. customAfter removal of the solvents
  7. customthe crude material was triturated with 40 mL of DCM

Sources & evidence

ORD record
ord-64e2c143a486468fb1914509aa94df46
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Linked notes

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