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

HRID 271704Notes

Reaction equation

HRID 271704 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-d6e5ce41cbd94d4b817f088f7df52584
Source dataset
uspto-grants-2008_11
Patent number
US07452911B2

Reaction notes

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