Triethylamine → 3-(4-Chloro-phenyl)-6-trimethylsilanylethynyl-pyridazine

HRID 1916670Notes

Reaction equation

HRID 1916670 reaction equation
C(N(CC)CC)C.[C:8]([Si:10]([CH3:13])([CH3:12])[CH3:11])#[CH:9].Cl[C:15]1[N:16]=[N:17][C:18]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[CH:19][CH:20]=1>C(#N)C.C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].[Cu]I>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([C:18]2[N:17]=[N:16][C:15]([C:9]#[C:8][Si:10]([CH3:13])([CH3:12])[CH3:11])=[CH:20][CH:19]=2)=[CH:26][CH:25]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 122575023-Chloro-6-(4-chlorophenyl)pyridazine

Product 1

HCID 673622923-(4-Chloro-phenyl)-6-trimethylsilanylethynyl-pyridazine

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere 3.48 mL (25.0 mmol) triethylamine and 2.08 mL (15.0 mmol) ethynyl-trimethyl-silane are added successively to a solution of 2.25 g (10.0 mmol) 3-chloro-6-(4-chloro-phenyl)-pyridazine in 50 mL acetonitrile and 20 mL THF. Then 292 mg (0.40 mmol) Pd(dppf)Cl2 and 76 mg (0.40 mmol) CuI are added. The reaction solution is stirred overnight at RT. The solvent is eliminated i.vac. and further purification is carried out by column chromatography on silica gel (PE/EtOAc 1:1).

Workup

  1. customand further purification

Sources & evidence

ORD record
ord-6769e4aee5d84ff38a3148d9f023d6eb
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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