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Potassium Phosphate, Tribasic → 8-(4-(4-Cyclopentylphenyl)pyridine-2-yl)-2-methylbenzofuro[2,3-b]pyridine

HRID 1844926
ノート
印刷プレビュー

反応式

HRID 1844926 の反応式
[CH3:1][C:2]1[N:7]=[C:6]2[O:8][C:9]3[C:14](B4OC(C)(C)C(C)(C)O4)=[CH:13][CH:12]=[CH:11][C:10]=3[C:5]2=[CH:4][CH:3]=1.Cl[C:25]1[CH:30]=[C:29]([C:31]2[CH:36]=[CH:35][C:34]([CH:37]3[CH2:41][CH2:40][CH2:39][CH2:38]3)=[CH:33][CH:32]=2)[CH:28]=[CH:27][N:26]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.COCCOC>[CH:37]1([C:34]2[CH:35]=[CH:36][C:31]([C:29]3[CH:30]=[CH:25][N:26]=[C:27]([C:14]4[C:9]5[O:8][C:6]6[C:5]([C:10]=5[CH:11]=[CH:12][CH:13]=4)=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=6)[CH:28]=3)=[CH:32][CH:33]=2)[CH2:38][CH2:39][CH2:40][CH2:41]1
参加物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 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 901214882-Methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridineHCID 901215232-Chloro-4-(4-cyclopentylphenyl)pyridine

生成物 1

HCID 901215388-(4-(4-Cyclopentylphenyl)pyridine-2-yl)-2-methylbenzofuro[2,3-b]pyridine
収率 73.3%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixture of 2-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine (2.5 g, 8.09 mmol), 2-chloro-4-(4-cyclopentylphenyl)pyridine (2.29 g, 8.89 mmol), Pd2(dba)3 (0.148 g 0.162 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (0.266 g, 0.647 mmol), potassium phosphate (6.01 g, 28.3 mmol), DME (70 mL) and water (7 mL) was degassed with nitrogen and then refluxed overnight. The mixture was concentrated and extracted with ethyl acetate. The ethyl acetate layer was dried on Na2SO4 and then further purified by column chromatography using ethyl acetate in hexanes to give 8-(4-(4-cyclopentylphenyl)pyridine-2-yl)-2-methylbenzofuro[2,3-b]pyridine (2.4 g, 73% yield).

後処理

  1. customwas degassed with nitrogen
  2. temperaturerefluxed overnight
  3. concentrationThe mixture was concentrated
  4. extractionextracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried on Na2SO4
  6. customfurther purified by column chromatography

出典と根拠

ORDレコード
ord-8a34c93337f74e29a59844c46f0d084c
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08946697B1

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート