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Potassium Acetate → 2-(4-Methyl-3-nitro-phenyl)-6-[2-(trifluoromethyl)-3-pyridyl]imidazo[2,1-f]pyridazine

HRID 539807
ノート
印刷プレビュー

反応式

HRID 539807 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]2=[N:8][C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=3)=[CH:10][N:4]2[N:3]=1.CC1(C)C(C)(C)OB([C:29]2[C:30]([C:35]([F:38])([F:37])[F:36])=[N:31][CH:32]=[CH:33][CH:34]=2)O1.CC([O-])=O.[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].O.C(O)CCC>[CH3:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[N:8]=[C:5]3[N:4]([CH:10]=2)[N:3]=[C:2]([C:29]2[C:30]([C:35]([F:38])([F:37])[F:36])=[N:31][CH:32]=[CH:33][CH:34]=2)[CH:7]=[CH:6]3)=[CH:12][C:13]=1[N+:18]([O-:20])=[O:19]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 517044Potassium AcetateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 569244343-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)pyridineHCID 866678576-Chloro-2-(4-methyl-3-nitro-phenyl)imidazo[2,1-f]pyridazine

生成物 1

HCID 680890622-(4-Methyl-3-nitro-phenyl)-6-[2-(trifluoromethyl)-3-pyridyl]imidazo[2,1-f]pyridazine
収率 60%

試薬・触媒・溶媒 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 2631-Butanol溶媒HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

A 500 mL flask is charged with 6-chloro-2-(4-methyl-3-nitro-phenyl)imidazo[2,1-f]pyridazine (10.104 g, 0.035 mol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)pyridine (Journal of Organic Chemistry, 2011, 76, 1062) (13.38 g, 0.049 mol), KOAc (6.869 g, 0.07 mol), bis(dibenzylideneacetone)palladium(0) (2.01 g, 3.5 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (3.34 g, 0.007 mol), butanol (112 mL) and water (20 mL). The reaction mixture is heated at 90° C. for 4 hr. The reaction is filtered through celite and washed with EtOAc. The liquid layers are combined, concentrated onto celite and purified by silica gel chromatography (0-75% EtOAc in CH2Cl2) to give the title compound (7.98 g, 60% yield). LCMS (m/z)=400.4 [M+H]+, tR=2.76 min.

後処理

  1. filtrationThe reaction is filtered through celite
  2. washwashed with EtOAc
  3. concentrationconcentrated onto celite
  4. custompurified by silica gel chromatography (0-75% EtOAc in CH2Cl2)

出典と根拠

ORDレコード
ord-1cc09979ea154dd3a728a51d1e3b8152
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08871767B2

反応ノート

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