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

HRID 1844932Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1844932
[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][C:32]=2[F:37])[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.[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C1(C)C=CC=CC=1>[F:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[C:29]1[CH:30]=[CH:25][N:26]=[C:27]([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:28]=1

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 463120482-Chloro-4-(2-fluorophenyl)pyridineHCID 901214882-Methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine

Produkt 1

HCID 901214858-(4-(2-Fluorophenyl)pyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 44556509Tris(dibenzylideneacetone) palladiumKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

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-fluorophenyl)pyridine (2.25 g, 10.84 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 vessel with 200 mL of toluene. Potassium phosphate tribasic (6 g, 28.3 mmol) was then dissolved in 25 mL of water and was added to the reaction mixture. The reaction mixture was degassed with nitrogen then was heated to reflux overnight. 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-fluorophenyl)pyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine (2.247 g, 6.34 mmol, 70% yield) as a white solid.

Aufarbeitung

  1. additionwas added to the reaction mixture
  2. customThe reaction mixture was degassed with nitrogen
  3. temperaturethen was heated
  4. temperatureto reflux overnight
  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

Quellen und Nachweise

ORD-Eintrag
ord-a870bf7df44641eb9939dd405ba8c646
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946697B1

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