Triethylamine → 5-(4-Chlorophenyl)-2-trimethylsilanylethynylpyridine

HRID 1916547Notes

Reaction equation

HRID 1916547 reaction equation
C(N(CC)CC)C.[C:8]([Si:10]([CH3:13])([CH3:12])[CH3:11])#[CH:9].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[CH:23][C:24](I)=[N:25][CH:26]=2)=[CH:17][CH:16]=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:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:22]=[CH:23][C:24]([C:9]#[C:8][Si:10]([CH3:13])([CH3:12])[CH3:11])=[N:25][CH:26]=2)=[CH:19][CH:20]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 859698495-(4-Chlorophenyl)-2-iodopyridine

Product 1

HCID 673636115-(4-Chlorophenyl)-2-trimethylsilanylethynylpyridine

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

34.9 mL (250 mmol) triethylamine and 20.8 mL (150.0 mmol) ethynyl-trimethyl-silane are added successively to a solution of 34 g (110 mmol) 5-(4-chloro-phenyl)-2-iodo-pyridine in 300 mL acetonitrile and 150 mL THF under an argon atmosphere. Then 803 mg (1.10 mmol) Pd(dppf)Cl2 and 209 mg (1.10 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 8:2).

Workup

  1. customand further purification

Sources & evidence

ORD record
ord-7392dbf8dbeb4f5baa6824ebe05837cc
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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