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

HRID 552890노트

반응식

HRID 552890 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-2e8a0f4a0a3c4e919670f920ca86f001
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951949B2

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