吡啶 → N-(5-bromopyridin-3-yl)-2-methylpropanamide

HRID 82069

反应方程式

HRID 82069 反应方程式
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.N1C=CC=CC=1.[C:15](Cl)(=[O:19])[CH:16]([CH3:18])[CH3:17]>C(Cl)Cl>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][C:15](=[O:19])[CH:16]([CH3:18])[CH3:17])[CH:3]=[N:4][CH:5]=1

参与物

5

反应物 3

HCID 1049吡啶HCID 62325异丁酰氯HCID 8176815-溴-3-氨基吡啶

产物 1

HCID 68195778N-(5-bromopyridin-3-yl)-2-methylpropanamide收率 71%

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂2 次

反应条件

温度
0 °C

实验过程

3-Amino-5-bromo pyridine (XXX) (1 eq) was dissolved in DCM and cooled to 0° C. before adding pyridine (2.2 eq) and isobutyryl chloride (XXXI) (1.1 eq). The reaction mixture was stirred at r.t. for 15 h until TLC showed the reaction was complete. The reaction mixture was diluted with DCM and washed with water. The organic extract was dried, concentrated and purified by column chromatography using silica gel (100-200 mesh) to afford N-(5-bromopyridin-3-yl)isobutyramide (XXXII) as a off white solid, (71% yield). 1H NMR (CDCl3) δ ppm 8.55-8.35 (m, 3H), 7.32 (s, 1H), 2.59-2.48 (m, 1H), 1.28-1.27 (d, 6H); ESIMS found C9H11BrN2O m/z 243.05(M+H).

后处理

  1. washwashed with water
  2. extractionThe organic extract
  3. customwas dried
  4. concentrationconcentrated
  5. custompurified by column chromatography

来源与证据

ORD记录
ord-e2d0f47f2cd0488b90a841ec61e944bf
来源数据集
uspto-grants-2014_09
专利号
US08846714B2

关联笔记

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