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

HRID 1512081ノート

反応式

HRID 1512081 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

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) δ1.85-1.95 (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).

後処理

  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

出典と根拠

ORDレコード
ord-d6b15a09b7c94e32ba7807abc2ceb2e7
出典データセット
uspto-grants-2012_07
特許番号
US08217057B2

反応ノート

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