Sodium Carbonate → HCID 90389413, compound

HRID 1526607Notes

Reaction equation

HRID 1526607 reaction equation
Br[C:2]1[C:3](C#N)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:11](=[O:14])([O-])[O-:12].[Na+].[Na+].[C:17](B1OC(C)(C)C(C)(C)O1)([CH3:19])=[CH2:18]>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>[Cl:8][C:6]1[CH:7]=[C:2]([C:17]([CH3:19])=[CH2:18])[C:3]([C:11]([OH:12])=[O:14])=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 225912463-Bromo-5-chloropyridine-2-carbonitrile

Product 1

HCID 90389413HCID 90389413, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
90 °C

Procedure

A microwave glass vessel was charged with 3-bromo-5-chloropicolinonitrile (0.5 g, 2.3 mmol), tetrakis(triphenylphosphine)palladium(0) (0.13 g, 0.115 mmol) and sodium carbonate (0.731 g, 6.90 mmol). The vial was evacuated and back-filled with nitrogen. Dioxane (10 mL) and water (3 mL) were added. The reaction mixture was degassed and isopropenylboronic acid pinacol ester (0.474 ml, 2.53 mmol) was added. The reaction mixture was heated to 90° C. for 2 hs. The reaction mixture was partitioned between water and EtOAc. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was dissolved in EtOH (7 mL) and NaOH (5M, 3 mL). The solution was heated to 115° C. for 1.5 hrs. The reaction mixture was partitioned between water and EtOAc. The organic phase was discarded and the aq. phase was acidified with aq. 2 M HCl and extracted with EtOAc. The organic phase was dried over MgSO4 and concentrated under reduced pressure to obtain the title compound as a light-yellow solid (0.373 g, 82%). MS m/z=198.1 [M+H]+. Calculated for C9H8ClNO2: 197.024

Workup

  1. customThe vial was evacuated
  2. additionback-filled with nitrogen
  3. additionDioxane (10 mL) and water (3 mL) were added
  4. customThe reaction mixture was degassed
  5. customThe reaction mixture was partitioned between water and EtOAc
  6. dry with materialThe organic phase was dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved in EtOH (7 mL)
  9. temperatureThe solution was heated to 115° C. for 1.5 hrs
  10. customThe reaction mixture was partitioned between water and EtOAc
  11. extractionextracted with EtOAc
  12. dry with materialThe organic phase was dried over MgSO4
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1cb890e07854470b878613127127f49b
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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