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Sodium Carbonate → 1,1-dimethylethyl 7-{5-acetyl-2-[(2-pyrazinylmethyl)oxy]phenyl}-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

HRID 879995
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 879995
Br[C:2]1[CH:3]=[C:4]([C:16](=[O:18])[CH3:17])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[N:14][CH:13]=[CH:12][N:11]=1.CC1(C)C(C)(C)OB([C:27]2[CH:44]=[CH:43][C:30]3[CH2:31][CH2:32][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:34][CH2:35][C:29]=3[CH:28]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[C:16]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]2[CH:15]=[N:14][CH:13]=[CH:12][N:11]=2)=[C:2]([C:27]2[CH:44]=[CH:43][C:30]3[CH2:31][CH2:32][N:33]([C:36]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:37])[CH2:34][CH2:35][C:29]=3[CH:28]=2)[CH:3]=1)(=[O:18])[CH3:17]
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Komponenten

5

Edukt 3

HCID 10340Sodium 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 706653921-{3-Bromo-4-[(2-pyrazinylmethyl)oxy]phenyl}ethanone

Produkt 1

HCID 706651151,1-dimethylethyl 7-{5-acetyl-2-[(2-pyrazinylmethyl)oxy]phenyl}-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylateAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-{3-bromo-4-[(2-pyrazinylmethyl)oxy]phenyl}ethanone (0.2 g) and 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 (0.34 g) in DME (4 ml) was added aqueous sodium carbonate (2M, 0.98 ml). This was degassed with nitrogen for 15 min before adding Tetrakis (37 mg). The reaction was heated under reflux overnight. TLC indicated the reaction had gone to completion and so it was cooled, diluted with water and extracted with ethyl acetate. The combined organics were dried over sodium sulphate and concentrated in vacuo to yield a crude product which was purified by column chromatography, eluting with 0-18% ethyl acetate in hexane. The appropriate fractions were concentrated in vacuo to yield the title compound, 0.093 g, 30% yield.

Aufarbeitung

  1. customThis was degassed with nitrogen for 15 min
  2. additionbefore adding Tetrakis (37 mg)
  3. temperatureThe reaction was heated
  4. temperatureunder reflux overnight
  5. temperaturewas cooled
  6. additiondiluted with water
  7. extractionextracted with ethyl acetate
  8. dry with materialThe combined organics were dried over sodium sulphate
  9. concentrationconcentrated in vacuo
  10. customto yield a crude product which
  11. customwas purified by column chromatography
  12. washeluting with 0-18% ethyl acetate in hexane
  13. concentrationThe appropriate fractions were concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cd226a5b61254cfebbfc0560a470aab1
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08993560B2

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