Potassium Carbonate → HCID 58020178, compound

HRID 1632105Notes

Reaction equation

HRID 1632105 reaction equation
Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([CH3:10])[N:3]=1.[Cl:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].C(O)C.O.O1CCOCC1>[Cl:11][C:12]1[CH:17]=[C:16]([C:2]2[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([CH3:10])[N:3]=2)[CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 2734323(3-Chlorophenyl)boronic acidHCID 109655632-Bromo-3-methoxy-6-methylpyridine

Product 1

HCID 58020178HCID 58020178, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
180 °C

Procedure

To 2-bromo-3-methoxy-6-methylpyridine (0.2 g, 1.0 mmol), 3-chlorophenylboronic acid (1) (0.19 g, 1.2 mmol), PPh3 (0.13 g, 0.5 mmol), K2CO3 (0.06 g, 0.4 mmol) and Pd(OAc)2 (0.03 g, 0.12 mmol) was added dioxane (3 mL), and EtOH—H2O (1:1, 1.5 mL). Ar gas was bubbled through the stirred reaction for 5 min. The reaction was stirred at 180° C. for 15 m using microwave oven (Biotage Intiator II). The reaction was cooled to room temperature, concentrated, and H2O and dichloromethane (40 mL each) were added. The organic layer was separated and the aqueous layer was extracted with dichloromethane (2×25 mL). The combined organic extracts were dried with Na2SO4, filtered, and concentrated. The residue was purified by silica gel column chromatography using 1:1 dichloromethane-hexanes then dichloromethane to afford 0.19 g (81%) of I-243 as a viscous liquid.

Workup

  1. customAr gas was bubbled through the stirred reaction for 5 min
  2. temperatureThe reaction was cooled to room temperature
  3. concentrationconcentrated
  4. additionH2O and dichloromethane (40 mL each) were added
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with dichloromethane (2×25 mL)
  7. dry with materialThe combined organic extracts were dried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography
  11. customdichloromethane to afford 0.19 g (81%) of I-243 as a viscous liquid

Sources & evidence

ORD record
ord-9e100bd8c24743e7910491ac9746953f
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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