Water → 1,1-dimethylethyl 7-(3-{[(4-methyl-2-pyridinyl)methyl]oxy}-2-pyridinyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

HRID 63273

Reaktionsgleichung

Reaktionsgleichung von HRID 63273
Br[C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][N:11]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:25]2[CH:42]=[CH:41][C:28]3[CH2:29][CH2:30][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:32][CH2:33][C:27]=3[CH:26]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCOCC1.O.Cl[Pd]Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C(OCC)(=O)C>[CH3:16][C:14]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:9][O:8][C:7]2[C:2]([C:25]3[CH:42]=[CH:41][C:28]4[CH2:29][CH2:30][N:31]([C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])[CH2:32][CH2:33][C:27]=4[CH:26]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)[CH:15]=1

Komponenten

9

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 57505869tert-Butyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,4,5-tetrahydro-3H-benzo[d]azepine-3-carboxylateHCID 866705442-Bromo-3-{[(4-methyl-2-pyridinyl)methyl]oxy}pyridine

Produkt 1

HCID 706652431,1-dimethylethyl 7-(3-{[(4-methyl-2-pyridinyl)methyl]oxy}-2-pyridinyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24290Palladium ChlorideKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a degassed mixture of 2-bromo-3-{[(4-methyl-2-pyridinyl)methyl]oxy}pyridine (2.83 g), 1,1-dimethylethyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (4.54 g) and cesium carbonate (9.9 g) in dioxane:water (4:1, 40 ml) was added PdCl2.dppf (0.828 g). The reaction mixture was heated at 120° C. overnight. The reaction mixture was added to water and extraction was carried out with ethyl acetate. The organic layer was dried over sodium sulphate and the filtrate was concentrated in vacuo. The crude product was purified through silica, eluting with 0-40% ethyl acetate in hexane. Appropriate fractions were concentrated in vacuo to yield the title compound, 3.8 g (84%).

Aufarbeitung

  1. dry with materialThe organic layer was dried over sodium sulphate
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe crude product was purified through silica
  4. washeluting with 0-40% ethyl acetate in hexane
  5. concentrationAppropriate fractions were concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6b515ef1666142fa88156e73db3e63be
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447074B2

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