Ethanol → HCID 57437657, compound

HRID 606677Notes

Reaction equation

HRID 606677 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][CH2:26][CH2:27][CH3:28])[CH:20]=[CH:19][C:17]=1[NH2:18].C(=O)([O-])[O-].[K+].[K+].CCO>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=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][CH2:26][CH2:27][CH3:28]

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 35296022-(1,3,2-Dioxaborinan-2-yl)benzonitrileHCID 19381158HCID 19381158, compound

Product 1

HCID 57437657HCID 57437657, compoundYield 39.8%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

13.1 g (69.8 mmol) 2-(1,3,2-dioxaborinan-2-yl)benzonitrile, 16.3 g (63.4 mmol) 2-bromo-4-hexylaniline, 1.62 g (1.40 mmol) tetrakis(triphenylphosphine) palladium(0), and 23.6 g (171 mmol) potassium carbonate where refluxed in 250 ml toluene and 100 ml EtOH under N2 atmosphere for 20 hours. HPLC and TLC revealed almost complete consumption of the aniline. 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 hexanes added to crystallize the product as off white solids (7.05 g, 39.8% yield, GC-MS confirmed).

Workup

  1. customconsumption of the aniline
  2. temperatureThe reaction mixture was cooled
  3. washThe solids were washed with ethyl acetate
  4. customto remove organics from the collected base
  5. customThe filtrate was then evaporated down
  6. customdried on silica
  7. customThe sample was purified
  8. customThe product fractions were then evaporated down to a minimal amount and hexanes
  9. additionadded
  10. customto crystallize the product as off white solids (7.05 g, 39.8% yield, GC-MS confirmed)

Sources & evidence

ORD record
ord-fac8096d27dd4a9ea599469406f8a42b
Source dataset
uspto-grants-2011_03
Patent number
US07915415B2

Reaction notes

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