Tetrabutylammonium Fluoride → 3-(4-Chloro-phenyl)-6-ethynyl-pyridazine

HRID 1916671Notes

Reaction equation

HRID 1916671 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[N:27]=[N:28][C:29]([C:32]#[C:33][Si](C)(C)C)=[CH:30][CH:31]=2)=[CH:22][CH:21]=1>C(Cl)Cl>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[N:27]=[N:28][C:29]([C:32]#[CH:33])=[CH:30][CH:31]=2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 673622923-(4-Chloro-phenyl)-6-trimethylsilanylethynyl-pyridazine

Product 1

HCID 859696873-(4-Chloro-phenyl)-6-ethynyl-pyridazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.10 g (3.49 mmol) TBAF are added at 0° C. to a solution of 1.00 g (3.49 mmol) 3-(4-chloro-phenyl)-6-trimethylsilanylethynyl-pyridazine in 10 mL DCM. The ice bath is removed and the reaction solution is stirred for 30 min. Water is added and the aqueous phase is extracted with EtOAc. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac. The product is reacted without any further purification.

Workup

  1. customThe ice bath is removed
  2. additionWater is added
  3. extractionthe aqueous phase is extracted with EtOAc
  4. dry with materialThe organic phase is dried over MgSO4
  5. customThe product is reacted without any further purification

Sources & evidence

ORD record
ord-ff938ebd871b4c57badc031aea30ff81
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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