1,2-Dimethoxyethane → HCID 23434230, compound

HRID 639769Notes

Reaction equation

HRID 639769 reaction equation
C(COC)OC.[NH2:7][C:8]1[CH:15]=[CH:14][C:13](Br)=[CH:12][C:9]=1[C:10]#[N:11].[F:17][C:18]([F:29])([F:28])[C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.O>[NH2:7][C:8]1[CH:15]=[CH:14][C:13]([C:22]2[CH:23]=[CH:24][C:19]([C:18]([F:29])([F:28])[F:17])=[CH:20][CH:21]=2)=[CH:12][C:9]=1[C:10]#[N:11]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 4297402-Amino-5-bromobenzonitrileHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 23434230HCID 23434230, compound

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent2×

Procedure

To dimethoxyethane (100 mL) and water (50 mL) was added 2-amino-5-bromo-benzonitrile (8.1 g), 4-trifluoromethyl-phenyl-boronic acid (8.6 g) and potassium carbonate (18.7 g), nitrogen was bobbled through the mixture for 10 minutes. Under a nitrogen atmosphere was bis(triphenyl-phosphine)palladium (II) chloride (0.3 g) added, the reaction mixture was heated at reflux overnight, then cooled to room temperature and added water (150 mL). The mixture was extracted with ethyl acetate, the organic phase was washed with water (50 mL) and brine (50 mL), then dried with magnesium sulfate and evaporated to an oil. The product was purified by column chromatography. Yield 8.36 g of white powder. Similarly was made:

Workup

  1. additionadded
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux overnight
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic phase was washed with water (50 mL) and brine (50 mL)
  6. dry with materialdried with magnesium sulfate
  7. customevaporated to an oil
  8. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-f57aad2b2cf9405fb0af2983f34cf1f3
Source dataset
uspto-grants-2010_04
Patent number
US07691891B2

Reaction notes

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