Cesium fluoride → N-(3,5-Bis-trifluoromethyl-benzyl)-N-(9-methyl-7-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamide

HRID 2353918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2353918
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]([CH:11]1[CH2:17][CH2:16][CH2:15][NH:14][C:13]2[C:18](Br)=[CH:19][C:20]([C:22]([F:25])([F:24])[F:23])=[CH:21][C:12]1=2)[C:8](=[O:10])[CH3:9].[CH3:36]B(O)O.[F-].[Cs+]>O1CCOCC1>[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]([CH:11]1[CH2:17][CH2:16][CH2:15][NH:14][C:13]2[C:18]([CH3:36])=[CH:19][C:20]([C:22]([F:25])([F:24])[F:23])=[CH:21][C:12]1=2)[C:8](=[O:10])[CH3:9]

Komponenten

5

Edukt 3

HCID 25953Cesium fluorideHCID 139377Methylboronic AcidHCID 86616074N-(3,5-Bis-trifluoromethyl-benzyl)-N-(9-bromo-7-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamide

Produkt 1

HCID 86616073N-(3,5-Bis-trifluoromethyl-benzyl)-N-(9-methyl-7-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamideAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of N-(3,5-Bis-trifluoromethyl-benzyl)-N-(9-bromo-7-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamide (0.0830 g, 0.144 mmol), methyl boronic acid (0.0260 g, 0.432 mmol) and cesium fluoride (0.0770 mg, 0.504 mmol) in dioxane (2.00 ml) was purged with nitrogen for 10 minutes. To it was added PdCl2(dppf) (0.0170 g) in one portion. The mixture was heated at 80° C. overnight. The solid was removed by filtration, washed with ethyl acetate (30.0 ml) and the filtrate was concentrated in vacuo. Purification by silica gel chromatography (gradient eluent, 0-40% ethyl acetate in hexane) provided the titled compound (0.0460 g, 63%) as white solid. MS (ES+): 513 (M+H).

Aufarbeitung

  1. customwas purged with nitrogen for 10 minutes
  2. additionTo it was added PdCl2(dppf) (0.0170 g) in one portion
  3. customThe solid was removed by filtration
  4. washwashed with ethyl acetate (30.0 ml)
  5. concentrationthe filtrate was concentrated in vacuo
  6. customPurification by silica gel chromatography (gradient eluent, 0-40% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-8a8553be79fd42ebae2157c49f45195b
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07749992B2

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