Potassium Carbonate → HCID 58092281, compound

HRID 1918476Notes

Reaction equation

HRID 1918476 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:16]=[C:15](B2OC(C)(C)C(C)(C)O2)[CH:14]=[CH:13][N:12]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.Cl[Pd]Cl>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([C:15]2[CH:14]=[CH:13][N:12]=[C:11]([O:10][CH3:9])[CH:16]=2)=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 8170982-Bromo-5-chloropyridineHCID 447548622-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Product 1

HCID 58092281HCID 58092281, compoundYield 34.6%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromo-5-chloropyridine (2.04 g, 10.6 mmol), 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (2.50 g, 10.6 mmol), K2CO3 (4.38 g, 31.8 mmol) and PdCl2 (dppf) (0.40 g, 0.53 mmol) were stirred in DMSO (20 mL). The reaction mixture was degassed, then back-filled with N2. The reaction mixture was stirred at 80° C. in a pre-heated oil bath for 2 hours. After cooling, the reaction was quenched with water and extracted with CH2Cl2. The organic layer was washed with H2O and 5% LiCl, dried with Na2SO4, filtered and concentrated. Flash chromatography (silica gel, hexanes/EtOAc), 100:0 to 50:50) afforded the title compound (810 mg, 34%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 8.67 (d, J=2.0 Hz, 1H), 8.27 (d, J=5.3 Hz, 1H), 7.79-7.75 (dd, J=8.8, 2.3 Hz, 1H), 7.70 (d, J=8.3 Hz, 1H), 7.46-7.44 (dd, J=5.3, 1.5 Hz, 1H), 7.30 (s, 1H), 3.99 (s, 3H).

Workup

  1. customThe reaction mixture was degassed
  2. additionback-filled with N2
  3. temperatureAfter cooling
  4. customthe reaction was quenched with water
  5. extractionextracted with CH2Cl2
  6. washThe organic layer was washed with H2O and 5% LiCl
  7. dry with materialdried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1cf807f32f1d4fa8b45d90e6647dc048
Source dataset
uspto-grants-2013_12
Patent number
US08618299B2

Reaction notes

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