Potassium Carbonate → HCID 90403125, compound

HRID 1049345Notes

Reaction equation

HRID 1049345 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].[CH3:26][N:27]1[CH:31]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:29]=[N:28]1.Cl[C:42]1[CH:47]=[C:46]([O:48][C:49]2[CH:50]=[CH:51][C:52]([NH2:59])=[N:53][C:54]=2[C:55]([F:58])([F:57])[F:56])[CH:45]=[CH:44][N:43]=1>O1CCOCC1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:26][N:27]1[CH:31]=[C:30]([C:44]2[CH:45]=[C:46]([O:48][C:49]3[CH:50]=[CH:51][C:52]([NH2:59])=[N:53][C:54]=3[C:55]([F:56])([F:57])[F:58])[CH:47]=[CH:42][N:43]=2)[CH:29]=[N:28]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 90403179HCID 90403179, compound

Product 1

HCID 90403125HCID 90403125, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A suspension of triphenylphosphine (0.033 g, 0.125 mmol), K2CO3 (0.118 g, 0.856 mmol), Pd(OAc)2 (0.007 g, 0.031 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyrazole (0.089 g, 0.428 mmol) and 5-((2-chloropyridin-4-yl)oxy)-6-(trifluoromethyl)pyridin-2-amine (0.062 g, 0.214 mmol) in dioxane (6 mL) and water (1.5 mL) was sparged with Ar and heated at 85° C. overnight. The mixture was cooled to RT, treated with brine, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4, concentrated and purified via silica gel chromatography (MeOH/EtOAc) to afford 5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)-6-(trifluoromethyl)pyridin-2-amine (55 mg, 77%). MS (ESI) m/z: 336.1 (M+H+).

Workup

  1. customwas sparged with Ar
  2. temperatureThe mixture was cooled to RT
  3. additiontreated with brine
  4. extractionextracted with EtOAc (3×)
  5. dry with materialthe combined organics were dried over Na2SO4
  6. concentrationconcentrated
  7. custompurified via silica gel chromatography (MeOH/EtOAc)

Sources & evidence

ORD record
ord-6abb863ff65a45f4ad7b34d4c2b7aa50
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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