Hydrogen Bromide → 5-bromo-2-(3-fluoro-4-hydroxyphenylamino)-N-phenylnicotinamide

HRID 606143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 606143
[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24]C)=[C:20]([F:26])[CH:19]=2)=[C:6]([CH:16]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:8].Br>CC(O)=O>[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([F:26])[CH:19]=2)=[C:6]([CH:16]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:8]

Komponenten

4

Edukt 2

HCID 260Hydrogen BromideHCID 597811305-bromo-2-(3-fluoro-4-methoxyphenylamino)-N-phenylnicotinamide

Produkt 1

HCID 597811355-bromo-2-(3-fluoro-4-hydroxyphenylamino)-N-phenylnicotinamideAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

This process was repeated with 5-bromo-2-(3-fluoro-4-methoxyphenylamino)-N-phenylnicotinamide (2.78 g, 6.7 mmol), HOAc (7 ml), and hydrobromic acid (48%, 23 ml, 424 mmol). Both reactions were combined, and the pH of the aqueous phase was raised to above 12, and then washed with DCM. Then, the pH of the aqueous phase was lowered to 6 with concentrated HCl, and the aqueous phase was extracted with 10:1 DCM/MeOH). The organic extracts were combined and concentrated to afford the desired 5-bromo-2-(3-fluoro-4-hydroxyphenylamino)-N-phenylnicotinamide (2.45 g, 6.10 mmol, 70% purity, 52% yield). MS (ESI pos. ion) m/z: 402 (MH+, 79Br), 404 (MH+, 81Br). Calc'd exact mass for C18H13BrFN3O2: 401 (79Br), 403 (81Br).

Aufarbeitung

  1. temperaturethe pH of the aqueous phase was raised to above 12
  2. washwashed with DCM
  3. extractionthe aqueous phase was extracted with 10:1 DCM/MeOH)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-63ae77092089449180833503888370ac
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915287B2

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