Cesium carbonate → HCID 86677036, compound

HRID 927121Notes

Reaction equation

HRID 927121 reaction equation
[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12]([CH:23]=[CH2:24])=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:32]1[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[C:34]([C:42]([F:45])([F:44])[F:43])[CH:33]=1>>[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12](/[CH:23]=[CH:24]/[C:37]2[CH:32]=[CH:33][C:34]([C:42]([F:43])([F:45])[F:44])=[C:35]([C:38]([F:39])([F:41])[F:40])[CH:36]=2)=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 457904804-Chloro-1,2-bis(trifluoromethyl)benzeneHCID 86677037HCID 86677037, compound2×

Product 1

HCID 86677036HCID 86677036, compound

Conditions

Temperature
140 °C

Procedure

3,4-bis(Benzyloxy)-6-ethenylpyridazine (Intermediate 78: 0.578 g, 1.816 mmol), cesium carbonate (0.887 g, 2.72 mmol), dichloropalladiumtricyclohexylphosphane (1:2) (0.067 g, 0.091 mmol) and 4-chloro-1,2-bis(trifluoromethyl)benzene (0.542 g, 2.179 mmol) were combined. The reaction vessel was evacuated and purged with nitrogen before toluene (6.05 ml) was added under vacuum and the whole was stirred under nitrogen and heated to 140° C. for 11 hours. Upon quenching with saturated aqueous ammonium chloride, the resulting mixture was diluted with dichloromethane, passed through a phase separator and concentrated in vacuo. The residue was purified by column chromatography eluting (silica, 0-50% ethyl acetate in petrol) to yield crude 3,4-bis(benzyloxy)-6-[(E)-2-[3,4-bis(trifluoromethyl)phenyl]-ethenyl]-pyridazine which was used directly in the next step without further purification.

Workup

  1. customThe reaction vessel was evacuated
  2. custompurged with nitrogen before toluene (6.05 ml)
  3. additionwas added under vacuum
  4. customUpon quenching with saturated aqueous ammonium chloride
  5. additionthe resulting mixture was diluted with dichloromethane
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography
  8. washeluting (silica, 0-50% ethyl acetate in petrol)

Sources & evidence

ORD record
ord-79310324b0e6458496d474097288e065
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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