Cesium carbonate → HCID 68210800, compound

HRID 1747530Notes

Reaction equation

HRID 1747530 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([CH:8]([OH:13])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[CH3:14][N:15]1[CH:19]=[C:18](B2OC(C)(C)C(C)(C)O2)[CH:17]=[N:16]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[F:10][C:9]([F:12])([F:11])[CH:8]([C:5]1[CH:6]=[N:7][C:2]([C:18]2[CH:17]=[N:16][N:15]([CH3:14])[CH:19]=2)=[CH:3][CH:4]=1)[OH:13]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 75806TricyclohexylphosphineHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 713019861-(6-Bromopyridin-3-yl)-2,2,2-trifluoroethan-1-ol

Product 1

HCID 68210800HCID 68210800, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

In 1,4-dioxane (2.0 mL) was dissolved 1-(6-bromopyridin-3-yl)-2,2,2-trifluoroethanol (98.6 mg, 0.385 mmol). To the solution were added 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (120 mg, 0.578 mmol), cesium carbonate (188 mg, 0.578 mmol), tris(dibenzylideneacetone)dipalladium (5.3 mg, 0.0058 mmol), tricyclohexylphosphine (3.9 mg, 0.0139 mmol) and water (0.2 mL), and the mixture was stirred at 80° C. for 2 hours. Water was added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=19/1) to give Compound A26 (94.5 mg, 950 yield).

Workup

  1. extractionExtraction with ethyl acetate
  2. washwashing with saturated brine
  3. dry with materialdrying over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent in the filtrate was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform/methanol=19/1)
  7. customto give Compound
  8. customA26 (94.5 mg, 950 yield)

Sources & evidence

ORD record
ord-2b66feef6cbe49fda5abb810dbcb5409
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

Loading…