N-bromobutanimide → 5-Bromo-3-(2,6-dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine

HRID 1169703노트

반응식

HRID 1169703 반응식
[Cl:1][C:2]1[C:16]([F:17])=[CH:15][CH:14]=[C:13]([Cl:18])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([NH2:12])=[N:8][CH:9]=[CH:10][CH:11]=1.[Br:19]N1C(=O)CCC1=O>C(#N)C>[Br:19][C:10]1[CH:11]=[C:6]([O:5][CH2:4][C:3]2[C:13]([Cl:18])=[CH:14][CH:15]=[C:16]([F:17])[C:2]=2[Cl:1])[C:7]([NH2:12])=[N:8][CH:9]=1

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 211114003-(2,6-Dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine

생성물 1

HCID 211114855-Bromo-3-(2,6-dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine수율 51%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
0 °C

실험 절차

A stirring solution of 3-(2,6-dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine (9.07 g, 0.03 mol) in acetonitrile was cooled to 0° C. using an ice bath. To this solution was added N-bromosuccinimide (NBS) (5.33 g, 0.03 mol) portionwise. The reaction was stirred at 0° C. for 15 min. The reaction was concentrated to dryness under vacuum. The resulting dark oil was dissolved in EtOAc (500 mL), and purified via silica gel chromatography. The solvents were then removed in vacuo to yield 5-bromo-3-(2,6-dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine (5.8 g, 0.015 mol, 51%) as a white crystalline solid. 1H NMR (CDCl3, 300 MHz) 1.85-1.95 (d, 3H), 4.7-5.0 (brs, 2H), 5.9-6.01 (q, 1H), 6.8-6.95 (d, 1H), 7.01-7.2 (t, 1H), 7.4-7.45 (m, 1H), 7.8-7.85 (d, 1H).

후처리

  1. concentrationThe reaction was concentrated to dryness under vacuum
  2. dissolutionThe resulting dark oil was dissolved in EtOAc (500 mL)
  3. custompurified via silica gel chromatography
  4. customThe solvents were then removed in vacuo

출처 및 근거

ORD 기록
ord-46ace9103c294fd2993cd61022f0db66
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07825137B2

반응 노트

불러오는 중…