Potassium Phosphate, Tribasic → 2-Methyl-8-(4-phenyl-2-pyridinyl)benzofuro[2,3-b]pyridine

HRID 1844936노트

반응식

HRID 1844936 반응식
[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][CH:34]=[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.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]=[C:29]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[CH:28]=[CH:27][N:26]=4)=[CH:13][CH:12]=[CH:11][C:10]=3[C:5]2=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 27628422-Chloro-4-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

생성물 1

HCID 901214912-Methyl-8-(4-phenyl-2-pyridinyl)benzofuro[2,3-b]pyridine수율 78%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

A mixture of 2-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine (4.34 g, 14.03 mmol), 2-chloro-4-phenylpyridine (2.66 g, 14.03 mmol), Pd2(dba)3 (0.257 g 0.281 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (0.582 g, 1.42 mmol), potassium phosphate (8.93 g, 42.1 mmol), toluene (180 mL) and water (28 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 2-methyl-8-(4-phenylpyridin-2-yl)benzofuro[2,3-b]pyridine (3.66 g, 10.88 mmol, 78% yield).

후처리

  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

출처 및 근거

ORD 기록
ord-9fccab714454466cb3f286fb38c551c9
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946697B1

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