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

HRID 1844926
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HRID 1844926 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][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
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참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

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).

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-8a34c93337f74e29a59844c46f0d084c
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08946697B1

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