Ethyl Acetate → HCID 67107011, compound

HRID 1026618Notes

Reaction equation

HRID 1026618 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][N:7]=[C:6](Cl)[CH:5]=1.[NH:12]1[C:20]2[C:15](=[CH:16][C:17](B(O)O)=[CH:18][CH:19]=2)[CH:14]=[CH:13]1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=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>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:17]2[CH:16]=[C:15]3[C:20](=[CH:19][CH:18]=2)[NH:12][CH:13]=[CH:14]3)[CH:5]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 27343615-Indolylboronic acidHCID 2736842Methyl 2-chloropyridine-4-carboxylate

Product 1

HCID 67107011HCID 67107011, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

2-Chloroisonicotinic acid methyl ester (1.22 g, 7.11 mmol), 1H-indole-5-boronic acid (1.15 g, 7.13 mmol), 2M-aqueous sodium carbonate solution (10 mL, 20 mmol) and tetrakis(triphenylphosphine)palladium (0.41 g, 0.35 mmol) were dissolved in toluene (140 mL), and stirred for 12 h under reflux. After completion of the reaction, ethyl acetate (200 mL) was added, and washed with aqueous sodium chloride solution. The organic layer was separated, dried over anhydrous magnesium sulfate, concentrated under reduced pressure and purified by column chromatography to give the title compound (440 mg, 1.74 mmol, 25% Yield).

Workup

  1. temperatureunder reflux
  2. additionwas added
  3. washwashed with aqueous sodium chloride solution
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-1355a1dc849a4e0c8d43fc4122e982ab
Source dataset
uspto-grants-2014_05
Patent number
US08729273B2

Reaction notes

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