Potassium Phosphate, Tribasic → HCID 90426054, compound

HRID 2279042Notes

Reaction equation

HRID 2279042 reaction equation
[Br:1][C:2]1[C:3]([O:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13](Cl)[CH:12]=2)=[CH:4][C:5]([F:9])=[C:6]([CH:8]=1)[NH2:7].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:26][N:27]1[CH:31]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:29]=[N:28]1>CN(C=O)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>[Br:1][C:2]1[C:3]([O:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([C:30]3[CH:29]=[N:28][N:27]([CH3:26])[CH:31]=3)[CH:12]=2)=[CH:4][C:5]([F:9])=[C:6]([CH:8]=1)[NH2:7]

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 90427659HCID 90427659, compound

Product 1

HCID 90426054HCID 90426054, compoundYield 52.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-bromo-4-((2-chloropyridin-4-yl)oxy)-2-fluoroaniline (994 mg, 3.13 mmol), K3PO4 (1.993 g, 9.39 mmol) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (716 mg, 3.44 mmol) in DMF (10 mL) and water (1.5 mL) was sparged with Ar, treated with Pd(PPh3)4 (362 mg, 0.313 mmol) and heated at 90° C. overnight. The mixture was cooled to RT, diluted with water, extracted with EtOAc (2×) and the combined organics were washed with brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford 5-bromo-2-fluoro-4-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)aniline (594 mg, 52%). MS (ESI) m/z: (M+H+): 363.0.

Workup

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

Sources & evidence

ORD record
ord-e949e84df492410da52e1be7637fc4dc
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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