Potassium Carbonate → HCID 68284597, compound

HRID 1527529Notes

Reaction equation

HRID 1527529 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[N:3]=1.[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.CCOC(C)=O.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>[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=1[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[N:3]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 14158462-bromo-6-nitropyridineHCID 27343362,6-Difluorophenylboronic acid2×

Product 1

HCID 68284597HCID 68284597, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-bromo-6-nitropyridine [21203-78-1] (200 mg, 0.99 mmol) and 2,6-difluorophenylboronic acid [162101-25-9] (311 mg, 1.97 mmol) in dioxane (4 mL) and water (1 mL) was added potassium carbonate (340 mg, 2.46 mmol) and Pd(PPh3)4 (114 mg, 0.099 mmol). The solution was heated for 60 min at 120° C. under microwave irradiation. More 2,6-difluorophenylboronic acid (622 mg, 3.94 mmol) was added to the mixture followed by heating at 120° C. for 120 min under microwave irradiation. The reaction mixture was then diluted with EtOAc and the resulting solution was washed successively with saturated aqueous NaHCO3 solution and brine, the organics were then dried (Phase separator) and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc 9:1) to give the title compound. MS (LC-MS): 237 [M+H]+, 259 [M+Na]+; tR (HPLC conditions k): 3.44 min.

Workup

  1. temperatureby heating at 120° C. for 120 min under microwave irradiation
  2. washthe resulting solution was washed successively with saturated aqueous NaHCO3 solution and brine
  3. customthe organics were then dried (Phase separator)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc 9:1)

Sources & evidence

ORD record
ord-ff6d850460b1433e9b2a239b7487cd60
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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