Pyridine → N-[3-Bromo-2-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-4-cyclopropyl-2-methyl-benzamide

HRID 2245728Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2245728
[Br:1][C:2]1[C:3]([C:9]([CH3:17])([CH3:16])[O:10][SiH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[CH:24]1([C:27]2[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[C:29]([CH3:36])[CH:28]=2)[CH2:26][CH2:25]1>C1(C)C=CC=CC=1.CCCCCC>[Br:1][C:2]1[C:3]([C:9]([CH3:17])([CH3:16])[O:10][SiH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:4]([NH:8][C:31](=[O:32])[C:30]2[CH:34]=[CH:35][C:27]([CH:24]3[CH2:26][CH2:25]3)=[CH:28][C:29]=2[CH3:36])[CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 592165404-Cyclopropyl-2-methylbenzoyl chlorideHCID 178455443HCID 178455443, Verbindung

Produkt 1

HCID 137328400N-[3-Bromo-2-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-4-cyclopropyl-2-methyl-benzamideAusbeute 98,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of [3-bromo-2-(tert-butyl-dimethyl-silanyloxymethyl)-phenylamine (21.28 g, 67.3 mmol) and anhydrous pyridine (6.5 mL, 80 mmol) in 50 mL of anhydrous toluene was added a solution of 4-cyclopropyl-2-methylbenzoyl chloride (13.25 g, 68.1 mmol) in 50 mL anhydrous toluene dropwise. A precipitate formed immediately upon addition. Stirred the mixture at ambient temperature under nitrogen overnight. Diluted the reaction mixture with 125 mL hexane and filtered off the precipitate. Washed the filtrate with 2×200 mL 1.0 M KHSO4, 2×200 mL 5% NaHCO3, and 250 mL water. Dried the solution over MgSO4 and concentrated in vacuo to obtain N-[3-Bromo-2-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-4-cyclopropyl-2-methyl-benzamide as a waxy light brown solid (31.54 g, 66.4 mmol). MS (ESI) 474, 476.0 (M+H)+.

Aufarbeitung

  1. customA precipitate formed immediately upon addition
  2. filtrationfiltered off the precipitate
  3. washWashed the filtrate with 2×200 mL 1.0 M KHSO4, 2×200 mL 5% NaHCO3, and 250 mL water
  4. dry with materialDried the solution over MgSO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a37369a2728042c0b0f1e3f8266b1c0d
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07683064B2

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