Potassium Carbonate → HCID 18177722, compound

HRID 970334Notes

Reaction equation

HRID 970334 reaction equation
Cl[C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:11]B(O)O.C([O-])([O-])=O.[K+].[K+]>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.O1CCOCC1>[CH3:11][C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 5204002-Chloro-6-methylpyridine-3-carbonitrile

Product 1

HCID 18177722HCID 18177722, compoundYield 50.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A 100 mL round bottom flask equipped with a condenser was charged with 2-Chloro-6-methyl-nicotinonitrile (1 g, 6.55 mmol), MeB(OH)2 (216 mg, 7.22 mmol), K2CO3 (1.36 g, 19.67 mmol), and dioxane (33 mL), followed by Pd(PPh3)4 (758 mg, 0.66 mmol) under argon. The mixture was heated to reflux for 48 hours, and then cooled down to RT. The resulting mixture was concentrated in vacuo, treated with 1N HCl (150 mL), and extracted with EtOAc (100 mL), Et2O (50 mL). The aqueous layer was basified with 50% NaOH until PH=10, and then extracted with EtOAC (100 mL) three times. The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by silica gel chromatography (5-10% EtOAC/Hexane) to give F2A as a light yellow solid (440 mg). HPLC retention time=0.766 min./condition A, M+=133.

Workup

  1. customA 100 mL round bottom flask equipped with a condenser
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 48 hours
  4. concentrationThe resulting mixture was concentrated in vacuo
  5. additiontreated with 1N HCl (150 mL)
  6. extractionextracted with EtOAc (100 mL), Et2O (50 mL)
  7. extractionextracted with EtOAC (100 mL) three times
  8. dry with materialThe combined organic layer was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude residue was purified by silica gel chromatography (5-10% EtOAC/Hexane)

Sources & evidence

ORD record
ord-a3cf78b266cb4594b6671b19e9076d05
Source dataset
uspto-grants-2007_12
Patent number
US07312209B2

Reaction notes

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