Boron tribromide → 2-(2,5-Dichloro-pyrimidin-4-ylamino)-3-fluoro-phenol

HRID 1687639

Reaktionsgleichung

Reaktionsgleichung von HRID 1687639
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([O:15]C)=[CH:13][CH:12]=[CH:11][C:10]=2[F:17])[C:5]([Cl:18])=[CH:4][N:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:10]([F:17])=[CH:11][CH:12]=[CH:13][C:14]=2[OH:15])[C:5]([Cl:18])=[CH:4][N:3]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 86633994(2,5-Dichloro-pyrimidin-4-yl)-(2-fluoro-6-methoxy-phenyl)-amine

Produkt 1

HCID 866339952-(2,5-Dichloro-pyrimidin-4-ylamino)-3-fluoro-phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Into a 1-Neck round-bottom flask was added (2,5-Dichloro-pyrimidin-4-yl)-(2-fluoro-6-methoxy-phenyl)-amine (3.676 g, 0.013 mol) and CH2Cl2 (54 mL, 0.85 mol). The reaction mixture was cooled to −78° C. and 1.00 M of BBr3 in CH2Cl2 (51.0 mL) was added dropwise. The reaction mixture was allowed to warm to rt, was stirred for 6 hrs and was quenched with H2O. Title compound obtained as off-white solid. (3.497 g, 81%). HPLC purity 99%, LCMS 274.08 (M+H), 1H-NMR (DMSO-d6, 400 MHz) δ 10.37 (s, 1H), 9.13 (s, 1H), 8.33 (s, 1H), 7.22-7.16 (m, 1H), 6.79-6.72 (m, 2H).

Aufarbeitung

  1. temperatureto warm to rt
  2. customwas quenched with H2O

Quellen und Nachweise

ORD-Eintrag
ord-4e254976bb2d4f5aba9b61311c7061db
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148391B2

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