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

HRID 899447ノート

反応式

HRID 899447 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-6782666a01654857b7f373dcd1c5bbee
出典データセット
uspto-grants-2008_04
特許番号
US07354942B2

反応ノート

読み込み中…