Potassium Carbonate → HCID 86673609, compound

HRID 1023453Notes

Reaction equation

HRID 1023453 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[CH:8]=1)(C)C.[C:14]([N:22]=C=O)(=[O:21])C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[C:6]([C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([NH2:22])=[O:21])[CH:8]=1)#[CH:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 78210Benzoyl isocyanateHCID 21097263HCID 21097263, compound

Product 1

HCID 86673609HCID 86673609, compoundYield 5.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

4-Trimethylsilanylethynyl-pyridin-2-ylamine (7.8 g, 42 mmol) and benzoyl isocynate (12.2 g, 82.9 mmol) are added into DCM (350 mL). The reaction mixture is heated at 50° C. for 16 hrs. Then the solvent is removed and the residue is dissolved in ethanol (350 mL). Potassium carbonate (8.58 g, 62.2 mmol) is added and the mixture is heated at 80° C. for 1 hr. The solvent is removed and the residue is partitioned between water (100 mL) and EtOAc (100 mL). The aqueous layer is separated and extracted with EtOAc (2×100 mL). The organic layers are combined and concentrated to give the crude product. Purification by silica flash column chromatography using 33% EtOAc in hexanes affords 350 mg of the desired product.

Workup

  1. customThen the solvent is removed
  2. dissolutionthe residue is dissolved in ethanol (350 mL)
  3. temperaturethe mixture is heated at 80° C. for 1 hr
  4. customThe solvent is removed
  5. customthe residue is partitioned between water (100 mL) and EtOAc (100 mL)
  6. customThe aqueous layer is separated
  7. extractionextracted with EtOAc (2×100 mL)
  8. concentrationconcentrated
  9. customto give the crude product
  10. customPurification by silica flash column chromatography

Sources & evidence

ORD record
ord-3b4372717d8545ea8d09cabbabc4dfdb
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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