Cesium carbonate → 6-(3-(Trimethylsilyl)phenyl)picolinaldehyde

HRID 1472913Notes

Reaction equation

HRID 1472913 reaction equation
Br[C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH3:10][Si:11]([CH3:22])([CH3:21])[C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH3:10][Si:11]([CH3:22])([CH3:21])[C:12]1[CH:17]=[C:16]([C:2]2[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=2)[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27570096-Bromopyridine-2-carbaldehydeHCID 45771813-(Trimethylsilyl)phenylboronic acid

Product 1

HCID 247300856-(3-(Trimethylsilyl)phenyl)picolinaldehydeYield 86%

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 (25 mL) at ambient temperature was added 3-trimethylsilylphenylboronic acid (1.04 g, 5.38 mmol), cesium carbonate (2.7 mL, 5.4 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.088 g, 0.11 mmol). The solution was degassed (3× vacuum/purge N2) and heated to 80° C. overnight. The mixture was cooled to room temperature and partioned between water and CH2Cl2. The organic phase concentrated and purified by chromatography (10% EtOAc:hexanes) to provide 1.18 g (86%) of the title compound. MS (DCI30 ) m/z 256 (M+H).

Workup

  1. customThe solution was degassed
  2. custom(3× vacuum/purge N2)
  3. temperatureThe mixture was cooled to room temperature
  4. concentrationThe organic phase concentrated
  5. custompurified by chromatography (10% EtOAc:hexanes)

Sources & evidence

ORD record
ord-f338445faaea4960b387eebc1ada09f6
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

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