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

HRID 62089

반응식

HRID 62089 반응식
[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

참가 물질

5

반응물 3

HCID 1049PyridineHCID 62325Isobutyryl chlorideHCID 8176813-Amino-5-bromopyridine

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-3747284b4ba84703aa5eeb5965d85a6e
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09446035B2

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