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

HRID 1844934노트

반응식

HRID 1844934 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]=[C:33]([F:37])[C:32]=2[F:38])[CH:28]=[CH:27][N:26]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O.C1(C)C=CC=CC=1>[F:38][C:32]1[C:33]([F:37])=[CH:34][CH:35]=[CH:36][C:31]=1[C:29]1[CH:28]=[CH:27][N:26]=[C:25]([C:14]2[C:9]3[O:8][C:6]4[C:5]([C:10]=3[CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=4)[CH:30]=1

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 866319712-Chloro-4-(2,3-difluorophenyl)pyridineHCID 901214882-Methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine

생성물 1

HCID 901215948-(4-(2,3-Difluorophenyl)pyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine수율 35.6%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

2-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine (2.8 g, 9.06 mmol), 2-chloro-4-(2,3-difluorophenyl)pyridine (2.452 g, 10.87 mmol), tris(dibenzylideneacetone)palladium(0) (0.166 g, 0.181 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.297 g, 0.725 mmol) were charged into the reaction mixture with 200 mL of toluene. Potassium phosphate tribasic (5.76 g, 27.2 mmol) was dissolved in 25 mL of water then was charged into the reaction mixture. This mixture was degassed then heated to reflux for 18 hours. The reaction mixture was cooled to room temperature. The toluene layer was separated and was dried over magnesium sulfate. This mixture was filtered and concentrated under vacuum. The crude residue was passed through a silica gel column using 15-22.5% ethyl acetate/heptanes. The clean product fractions were evaporated under reduced pressure yielding 8-(4-(2,3-difluorophenyl)pyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine (1.2 g, 3.22 mmol, 35.6% yield) as a white solid.

후처리

  1. additionthen was charged into the reaction mixture
  2. customThis mixture was degassed
  3. temperaturethen heated
  4. temperatureto reflux for 18 hours
  5. customThe toluene layer was separated
  6. dry with materialwas dried over magnesium sulfate
  7. filtrationThis mixture was filtered
  8. concentrationconcentrated under vacuum
  9. customThe clean product fractions were evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-19669df0d28e48259e4176a87c1abffa
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946697B1

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