Boron tribromide → 4-[2-(5,8-Difluoroquinazolin-4-ylamino)-ethyl]-2-methylphenol

HRID 1467400Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1467400
[F:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]2[C:3]=1[C:4]([NH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22]C)=[C:18]([CH3:24])[CH:17]=1)=[N:5][CH:6]=[N:7]2.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]2[C:3]=1[C:4]([NH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH3:24])[CH:17]=1)=[N:5][CH:6]=[N:7]2

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 59222937(5,8-Difluoroquinazolin-4-yl)-[2-(4-methoxy-3-methylphenyl)-ethyl]-amine

Produkt 1

HCID 592229364-[2-(5,8-Difluoroquinazolin-4-ylamino)-ethyl]-2-methylphenolAusbeute 101,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (5,8-difluoroquinazolin-4-yl)-[2-(4-methoxy-3-methylphenyl)-ethyl]-amine (0.86 g, 2.6 mmol) in CH2Cl2 (10 mL) cooled to −50° C., was added 7.8 mL BBr3 (1 M in CH2Cl2, 7.8 mmol). The solution was allowed to warm to room temperature and stirred overnight, and then quenched slowly with methanol. The solvent was removed by rotary evaporation, and the residue was diluted with water and stirred for a few min. The pale yellow solid precipitate was collected by suction filtration, washed with water, and dried in vacuum at 50° C. overnight to give 0.83 g (quantitative yield) of 4-[2-(5,8-difluoroquinazolin-4-ylamino)-ethyl]-2-methylphenol. 1H NMR (d4-DMSO+d6-acetone): δ 9.5-8.5 (m, 3H), 7.97 (m, 1H), 7.61 (m, 1H), 6.99 (s, 1H), 6.91 (d, J=8.1 Hz, 1H), 6.75 (d, J=8.1 Hz, 1H), 3.92 (m, 2H), 2.88 (t, J=7.8 Hz, 2H), 2.11 (s, 3H). LC/MS: 316.04 (M++1). The product was used in the following reaction without further purification. M.P. 244-251° C.

Aufarbeitung

  1. customquenched slowly with methanol
  2. customThe solvent was removed by rotary evaporation
  3. additionthe residue was diluted with water
  4. stirringstirred for a few min
  5. filtrationThe pale yellow solid precipitate was collected by suction filtration
  6. washwashed with water
  7. customdried in vacuum at 50° C. overnight

Quellen und Nachweise

ORD-Eintrag
ord-466d15b35326429a892710289632be7c
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000162B2

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