Cesium carbonate → HCID 86671316, compound

HRID 1472919Notes

Reaction equation

HRID 1472919 reaction equation
Br[C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH2:10]([O:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][C:16]=1[Cl:24])[CH2:11][CH2:12][CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH2:10]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=2)=[CH:17][C:16]=1[Cl:24])[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27570096-Bromopyridine-2-carbaldehydeHCID 52012114-Butoxy-3-chlorophenylboronic acid

Product 1

HCID 86671316HCID 86671316, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-bromopicolinaldehyde (4.07 g, 21.88 mmol) in dioxane (40 mL) at ambient temperature was added 4-butoxy-3-chlorophenylboronic acid (5.00 g, 21.9 mmol), 2M cesium carbonate (22.0 mL, 43.8 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.357 g, 0.438 mmol). The mixture was degassed (3× vacuum/purge N2) then heated at 80° C. overnight. The mixture was cooled to room temperature then partioned between water and CH2Cl2. The organic phase was concentrated and purified by chromatography (silica gel, 10% ethyl acetate:hexanes) to provide 5.20 g (82%) of the title compound. MS (DCI+) m/z 290 (M+H).

Workup

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

Sources & evidence

ORD record
ord-c076464f47464263ac023e81e7af6b13
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

Loading…