Cesium carbonate → HCID 72942664, compound

HRID 1472921Notes

Reaction equation

HRID 1472921 reaction equation
Br[C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][C:16]=1[F:17].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[Cl:10][C:11]1[CH:12]=[C:13]([C:2]2[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=2)[CH:14]=[CH:15][C:16]=1[F:17]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 27570096-Bromopyridine-2-carbaldehyde

Product 1

HCID 72942664HCID 72942664, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-bromopicolinaldehyde (1.07 g, 5.74 mmol) in dioxane (30 mL) at ambient temperature was added 3-chloro-4-fluorophenylboronic acid (1.00 g, 5.74 mmol), 2M cesium carbonate (8.60 mL, 17.2 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.234 g, 0.287 mmol). The mixture was degassed (3× vacuum/purge N2), then heated at 80° C. overnight. After cooling to ambient temperature the mixture was concentrated and the residue was partitioned between water and CH2Cl2. The organic extract was concentrated and purified by chromatography (10% ethyl acetate:hexanes) to provide the title compound. MS (DCI+) m/z 236 (M+H).

Workup

  1. customThe mixture was degassed
  2. custom(3× vacuum/purge N2)
  3. temperatureAfter cooling to ambient temperature the mixture
  4. concentrationwas concentrated
  5. customthe residue was partitioned between water and CH2Cl2
  6. extractionThe organic extract
  7. concentrationwas concentrated
  8. custompurified by chromatography (10% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-7dfc44e926ce47209dd5f3865e35f633
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

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