Cesium carbonate → HCID 22240163, compound

HRID 891873Notes

Reaction equation

HRID 891873 reaction equation
Cl[C:2]1[N:3]=[N:4][CH:5]=[C:6]([O:8][CH3:9])[CH:7]=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+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>O1CCOCC1.C(OC(=O)C)C>[Cl:10][C:11]1[CH:12]=[C:13]([C:2]2[N:3]=[N:4][CH:5]=[C:6]([O:8][CH3:9])[CH:7]=2)[CH:14]=[CH:15][C:16]=1[F:17]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 109756123-Chloro-5-methoxypyridazine

Product 1

HCID 22240163HCID 22240163, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

3-Chloro-5-methoxy-pyridazine (Bryant, R. D.; Kunng, F.-A.; South, M. S. J. Heterocycl. Chem. (1995), 32(5), 1473-6.), 3-chloro-4-fluorophenylboronic acid, Cs2CO3 and tris(dibenzylideneacetone)dipalladium chloroform complex are mixed and a solution of tri-tert-butylphosphine in degassed dioxane is added. The mixture is heated at about 90° C. for 22 hours then cooled to room temperature, ethylacetate is added, the solid is filtered and the filtrate is concentrated in vacuo to provide 3-(3-chloro-4-fluoro-phenyl)-5-methoxy-pyridazine (a compound of formula XI).

Workup

  1. temperaturethen cooled to room temperature
  2. filtrationthe solid is filtered
  3. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-42be0ef4d16a42f093d639596df46db4
Source dataset
uspto-grants-2006_02
Patent number
US07005432B2

Reaction notes

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