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

HRID 1916670ノート

反応式

HRID 1916670 の反応式
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

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  1. customand further purification

出典と根拠

ORDレコード
ord-6769e4aee5d84ff38a3148d9f023d6eb
出典データセット
uspto-grants-2013_12
特許番号
US08618132B2

反応ノート

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