Cesium carbonate → HCID 86671318, compound

HRID 1472927Notes

Reaction equation

HRID 1472927 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:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[F:10][C:11]([F:25])([F:26])[C:12]1[CH:17]=[C:16]([C:18]([F:19])([F:20])[F:21])[CH:15]=[CH:14][C:13]=1[C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27570096-Bromopyridine-2-carbaldehydeHCID 27826672,4-Bis(trifluoromethyl)phenylboronic acid

Product 1

HCID 86671318HCID 86671318, compound

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 2,4-bis(trifluoromethyl)phenylboronic acid (1.38 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 to room temperature and concentrated and the residue then partitioned between water and CH2Cl2. The organic layer concentrated and purified by chromatography (20% ethyl acetate:hexanes) to provide the title compound.

Workup

  1. customThe mixture was degassed
  2. custom(3× vacuum/purge N2)
  3. temperatureThe mixture was cooled to room temperature
  4. concentrationconcentrated
  5. customthe residue then partitioned between water and CH2Cl2
  6. concentrationThe organic layer concentrated
  7. custompurified by chromatography (20% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-a58f63bda49b471fb19ea6b178ef896d
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

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