Tert-Butyl nitrite → 4,6-Dibromo-2-(2,4-difluorophenyl)-3-methylpyridine

HRID 394166노트

반응식

HRID 394166 반응식
[Br:1][C:2]1[C:7](N)=[C:6]([Br:9])[C:5]([CH3:10])=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])[N:3]=1.C(ON=O)(C)(C)C>C1COCC1>[Br:9][C:6]1[CH:7]=[C:2]([Br:1])[N:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])[C:5]=1[CH3:10]

참가 물질

4

반응물 2

HCID 10906Tert-Butyl nitriteHCID 226480972,4-Dibromo-6-(2,4-difluorophenyl)-5-methylpyridin-3-amine

생성물 1

HCID 226480394,6-Dibromo-2-(2,4-difluorophenyl)-3-methylpyridine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

To a stirred solution of 2,4-dibromo-6-(2,4-difluorophenyl)-5-methylpyridin-3-amine (10 g, 26.4 mmol, 1 eq) in THF (100 mL) was added tert-butylnitrite (4.7 mL, 39.6 mmol, 1.5 eq). The solution warmed and gas evolution was evident. After 2 h, the mixture was heated to and maintained at 60° C. for 45 min. The mixture was cooled and concentrated in vacuo. The product was purified by flash column chromatography eluting with 2% Et2O in hexanes to give 4,6-dibromo-2-(2,4-difluorophenyl)-3-methylpyridine. Mass spectrum (ESI) 362.2 (M+1); 364.2 (M+3); 366.2 (M+5).

후처리

  1. temperatureThe solution warmed
  2. temperaturethe mixture was heated to and
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by flash column chromatography
  6. washeluting with 2% Et2O in hexanes

출처 및 근거

ORD 기록
ord-08df8454c9504f4e9919912e2880ff64
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809199B2

반응 노트

불러오는 중…