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

HRID 889134

반응식

HRID 889134 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 (XVIII) (1 eq) was dissolved in DCM and cooled to 0° C. before adding pyridine (2.2 eq) and isobutyryl chloride (XIX) (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 (XX) 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-5cba7cac7c3140dcb823249f3b217b29
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252812B2

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