Potassium Phosphate, Tribasic → 2-Methyl-8-(5-phenyl-2-pyridinyl)benzofuro[2,3-b]pyridine

HRID 1844930ノート

反応式

HRID 1844930 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]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[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.C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:7]=[C:6]2[O:8][C:9]3[C:14]([C:25]4[CH:30]=[CH:29][C:28]([C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)=[CH:27][N:26]=4)=[CH:13][CH:12]=[CH:11][C:10]=3[C:5]2=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 27628682-Chloro-5-phenylpyridineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 901214882-Methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine

生成物 1

HCID 901216732-Methyl-8-(5-phenyl-2-pyridinyl)benzofuro[2,3-b]pyridine収率 42.3%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 1140Toluene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 (3.0 g, 9.70 mmol), 2-chloro-5-phenylpyridine (2.024 g, 10.67 mmol), Pd2(dba)3 (0.178 g 0.192 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (0.319 g, 0.776 mmol), potassium phosphate (7.21 g, 34.0 mmol), toluene (70 mL) and water (7 mL) was degassed with nitrogen and then refluxed overnight. It 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 2-methyl-8-(5-phenylpyridin-2-yl)benzofuro[2,3-b]pyridine (1.38 g, 4.10 mmol, 42.3% yield).

後処理

  1. customwas degassed with nitrogen
  2. temperaturerefluxed overnight
  3. concentrationIt 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-c5510a6857ab456ca187c14e7b28f700
出典データセット
uspto-grants-2015_02
特許番号
US08946697B1

反応ノート

読み込み中…