Cesium carbonate → HCID 24730073, compound

HRID 1472928Notes

Reaction equation

HRID 1472928 reaction equation
Br[C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[F:10][C:11]([F:26])([F:25])[C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[F:10][C:11]([F:25])([F:26])[C:12]1[CH:13]=[C:14]([C:2]2[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=2)[CH:15]=[C:16]([C:18]([F:19])([F:20])[F:21])[CH:17]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1562653,5-Bis-trifluoromethylphenylboronic acidHCID 27570096-Bromopyridine-2-carbaldehyde

Product 1

HCID 24730073HCID 24730073, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-bromopicolinaldehyde (1.00 g, 5.38 mmol) in dioxane (30 mL) at ambient temperature was added 3,5-bis(trifluoromethyl)phenylboronic acid (1.39 g, 5.38 mmol), 2M cesium carbonate (8.0 mL, 16 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.220 g, 0.269 mmol). The mixture was degassed (3× vacuum/purge N2), then heated at 80° C. overnight. The mixture was cooled, concentrated and the residue partitioned between water and CH2Cl2. The organic layer concentrated and purified by chromatography (10% ethyl acetate:hexanes) to provide 1.36 g (79%) of the title compound.

Workup

  1. customThe mixture was degassed
  2. custom(3× vacuum/purge N2)
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. customthe residue partitioned between water and CH2Cl2
  6. concentrationThe organic layer concentrated
  7. custompurified by chromatography (10% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-6bc388979ea7422e9cdef3d0674cce91
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

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