Ethanol → HCID 57437658, compound

HRID 606680Notes

Reaction equation

HRID 606680 reaction equation
O1CCCOB1[C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[C:9]#[N:10].Br[C:16]1[CH:22]=[C:21]([CH2:23][CH2:24][CH2:25][CH3:26])[CH:20]=[CH:19][C:17]=1[NH2:18].C(=O)([O-])[O-].[K+].[K+].C(O)C>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>[CH2:23]([C:21]1[CH:22]=[CH:16][C:17]2[C:19](=[C:7]3[C:8](=[C:9]([NH2:10])[N:18]=2)[CH:11]=[CH:12][CH:13]=[CH:14]3)[CH:20]=1)[CH2:24][CH2:25][CH3:26]

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 35296022-(1,3,2-Dioxaborinan-2-yl)benzonitrileHCID 193811342-Bromo-4-butylbenzenamine

Product 1

HCID 57437658HCID 57437658, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

20.0 g (87.7 mmol) 2-(1,3,2-dioxaborinan-2-yl)benzonitrile, 13.7 g (73.1 mmol) 2-bromo-4-butylaniline, 1.70 g (1.46 mmol) tetrakis(triphenylphosphine)palladium(0), and 27.2 g (198 mmol) potassium carbonate where refluxed in 400 mL toluene and 200 mL ethanol under N2 atmosphere for 20 h. HPLC and TLC revealed almost complete consumption of the aniline. An additional 1.8 g 2-(1,3,2-dioxaborinan-2-yl)benzonitrile was added and refluxed continued for an additional 18 h. The reaction mixture was cooled and passed through a filter. The solids were washed with ethyl acetate to remove organics from the collected base. The filtrate was then evaporated down and dried on silica. The sample was purified using silica gel chromatography with 100% ethyl acetate as the eluent. The product fractions were then evaporated down to a minimal amount and the product recrystallized from EtOAc/hexanes to give 12.0 g of the title compound as light yellow solids (65.9% yield, GC-MS confirmed).

Workup

  1. customconsumption of the aniline
  2. additionAn additional 1.8 g 2-(1,3,2-dioxaborinan-2-yl)benzonitrile was added
  3. temperaturerefluxed
  4. temperatureThe reaction mixture was cooled
  5. washThe solids were washed with ethyl acetate
  6. customto remove organics from the collected base
  7. customThe filtrate was then evaporated down
  8. customdried on silica
  9. customThe sample was purified
  10. customThe product fractions were then evaporated down to a minimal amount
  11. customthe product recrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-c07843101c8f4998aea7947fa11b6fd5
Source dataset
uspto-grants-2011_03
Patent number
US07915415B2

Reaction notes

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