Carbon tetrabromide → N-[4-(bromomethyl)-6-chloropyridin-2-yl]-N-propylmethanesulfonamide

HRID 552890Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 552890
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH2:13][CH2:14][CH3:15])[S:9]([CH3:12])(=[O:11])=[O:10])[CH:5]=[C:4]([CH2:16]O)[CH:3]=1.C(Br)(Br)(Br)[Br:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:19][CH2:16][C:4]1[CH:3]=[C:2]([Cl:1])[N:7]=[C:6]([N:8]([CH2:13][CH2:14][CH3:15])[S:9]([CH3:12])(=[O:11])=[O:10])[CH:5]=1

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 57775667N-[6-chloro-4-(hydroxymethyl)pyridin-2-yl]-N-propylmethanesulfonamide

Produkt 1

HCID 59650918N-[4-(bromomethyl)-6-chloropyridin-2-yl]-N-propylmethanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of N-[6-chloro-4-(hydroxymethyl)pyridin-2-yl]-N-propylmethanesulfonamide (740 mg, 2.65 mmol) in dichloromethane (20 mL) cooled to 0° C. was added carbon tetrabromide (967 mg, 2.92 mmol) and triphenylphosphine (765 mg, 2.92 mmol). After 10 min, the reaction mixture was allowed to warm to rt and stirred for 0.5 h. The reaction mixture was concentrated in vacuo and purified by flash chromatography (silica, 0-25% EtOAc/hexanes) to provide N-[4-(bromomethyl)-6-chloropyridin-2-yl]-N-propylmethanesulfonamide as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.34 (s, 1H), 7.22 (s, 1H), 4.35 (s, 2H), 3.85 (t, J=7.6 Hz, 2H), 3.04 (s, 3H), 1.64-1.50 (m, 2H), 0.93 (t, J=7.2 Hz, 3H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by flash chromatography (silica, 0-25% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2e8a0f4a0a3c4e919670f920ca86f001
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951949B2

Notizen zur Reaktion

Wird geladen…