Sodium Carbonate → HCID 86707215, compound

HRID 2408226Notes

Reaction equation

HRID 2408226 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[N:10]2)=[C:4]([F:18])[CH:3]=1.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:18][C:4]1[CH:3]=[C:2]([C:21]2[C:20]([NH2:19])=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:7]=[C:6]([F:8])[C:5]=1[N:9]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[N:10]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2773216(2-Aminophenyl)boronic acidHCID 86707216HCID 86707216, compound2×

Product 1

HCID 86707215HCID 86707215, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 1-(4-bromo-2,6-difluorophenyl)-3-(trifluoromethyl)-1H-pyrazole (i.e. the product of Step C, 1.83 g, 5.6 mmol), B-(2-aminophenyl)-boronic acid (0.90 g, 6.58 mmol), sodium carbonate (2.07 g, 19.5 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.33 g, 0.76 mmol) in 1,2-dimethoxyethane (46 mL) and water (11 mL) was heated at 85° C. for 16 h. The reaction mixture was then concentrated under reduced pressure, and the residue was purified by medium pressure liquid chromatography on silica gel eluted with 0 to 100% ethyl acetate in hexanes to yield the title compound (1.02 g).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customthe residue was purified by medium pressure liquid chromatography on silica gel
  3. washeluted with 0 to 100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-55827dc3232648c7a53a344a95ffcb2a
Source dataset
uspto-grants-2014_08
Patent number
US08815772B2

Reaction notes

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