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

HRID 394166ノート

反応式

HRID 394166 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-08df8454c9504f4e9919912e2880ff64
出典データセット
uspto-grants-2004_10
特許番号
US06809199B2

反応ノート

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