Potassium Carbonate → HCID 90403352, compound

HRID 1049353Notes

Reaction equation

HRID 1049353 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[N:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[F:24][C:25]([F:36])([F:35])[C:26]1[CH:31]=[C:30](B(O)O)[CH:29]=[CH:28][N:27]=1>O1CCOCC1.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>[N+:15]([C:12]1[N:11]=[CH:10][C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([C:30]3[CH:29]=[CH:28][N:27]=[C:26]([C:25]([F:36])([F:35])[F:24])[CH:31]=3)[CH:7]=2)=[CH:14][CH:13]=1)([O-:17])=[O:16]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 451588802-(Trifluoromethyl)pyridine-4-boronic acidHCID 593227792-Chloro-4-((6-nitropyridin-3-yl)oxy)pyridine

Product 1

HCID 90403352HCID 90403352, compoundYield 77.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of Example A1 (0.125 g, 0.497 mmol), Pd(PPh3)4 (0.029 g, 0.025 mmol), K2CO3 (0.275 g, 1.987 mmol) and 2-(trifluoromethyl)pyridine-4-boronic acid (0.104 g, 0.546 mmol) in dioxane (6 mL) and water (1.5 mL) was sparged with Ar and heated at 90° C. overnight. The mixture was cooled to RT, treated with satd. NaHCO3 and EtOAc and the solids were removed via filtration through diatomaceous earth. The layers of the filtrate were separated, the aqueous layer extracted with EtOAc (3×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford 4-((6-nitropyridin-3-yl)oxy)-2′-(trifluoromethyl)-2,4′-bipyridine (139 mg, 77%). 1H NMR (400 MHz, DMSO-d6): δ 8.89 (d, J=5.2 Hz, 1H), 8.78 (m, 1H), 8.64 (m, 1H), 8.53 (s, 1H), 8.44-8.38 (m, 2H), 8.17 (d, J=2.3 Hz, 1H), 8.03 (m, 1H), 7.36 (dd, J=5.5, 2.3 Hz, 1H); MS (ESI) m/z: 363.1 (M+H+).

Workup

  1. temperatureThe mixture was cooled to RT
  2. additiontreated with satd
  3. customNaHCO3 and EtOAc and the solids were removed via filtration through diatomaceous earth
  4. customThe layers of the filtrate were separated
  5. extractionthe aqueous layer extracted with EtOAc (3×)
  6. dry with materialthe combined organics were dried over Na2SO4
  7. concentrationconcentrated to dryness
  8. custompurified via silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-35401d50d3d74ef2853e0429ef95af25
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

Loading…