3,5-Dimethylbenzyl bromide → HCID 54407387, Verbindung

HRID 842935

Reaktionsgleichung

Reaktionsgleichung von HRID 842935
[CH2:1]([NH:4][C:5](=[O:17])[C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:8][CH:7]=1)[CH:2]=[CH2:3].CC1C=C(C=C(C)C=1)CBr>C1(C)C=CC=CC=1>[CH:1]([NH:4][C:5](=[O:17])[C:6]1[CH:7]=[CH:8][C:9]([O:12][C:13]([F:15])([F:16])[F:14])=[CH:10][CH:11]=1)=[CH:2][CH3:3]

Komponenten

4

Edukt 2

HCID 1413343,5-Dimethylbenzyl bromideHCID 22616308HCID 22616308, Verbindung

Produkt 1

HCID 54407387HCID 54407387, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Compound 11 (100 mg, 0.57 mmol) was combined with 3,5-dimethylbenzyl bromide (0.57 mmol) and heated in toluene to 100° C. for 2 hours. The resulting mixture was cooled and washed with aqueous sodium bicarbonate and extracted with methylene chloride. The organic extract was dried (sodium sulfate), filtered, and purified by silica gel chromatography (methylene chloride, methanol) to yield 12 (example 21) (65%). 1H NMR (400 MHz, CDCl3) δ8.57 (d, J=8.0 Hz, 1 H, Ar), 7.13 (dd, J=2.8, 9.2 Hz, 1 H, Ar), 6.99 (d, J=7.2 Hz, 1 H, Ar), 6.89 (s, 3 H, Ar), 6.85 (d, J=2.8 Hz, 1 H, Ar), 6.42 (d, J=7.2 Hz, 1 H, Ar), 5.36 (s, 2 H, CH2), 3.90 (s, 3 H, CH3O), 2.24 (s, 6 H, CH3); M/Z (ESI+) 293 ([M+H]+).

Aufarbeitung

  1. temperatureThe resulting mixture was cooled
  2. washwashed with aqueous sodium bicarbonate
  3. extractionextracted with methylene chloride
  4. extractionThe organic extract
  5. dry with materialwas dried (sodium sulfate)
  6. filtrationfiltered
  7. custompurified by silica gel chromatography (methylene chloride, methanol)

Quellen und Nachweise

ORD-Eintrag
ord-555db30bd7194e9394527049c5d52385
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06376530B1

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