N-Methoxy-N-methyl-6-(4-trifluoromethyl-phenyl)-nicotinamide → 4,4,4-Trifluoro-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-butan-1-one

HRID 1669304ノート

反応式

HRID 1669304 の反応式
CON(C)[C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[N:7][CH:6]=1.[F:23][C:24]([F:31])([F:30])[CH:25]([Mg]Br)[CH2:26]C>O1CCCC1>[F:23][C:24]([F:31])([F:30])[CH2:25][CH2:26][C:4]([C:5]1[CH:6]=[N:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:9][CH:10]=1)=[O:21]

参加物

4

反応物 2

HCID 86620355N-Methoxy-N-methyl-6-(4-trifluoromethyl-phenyl)-nicotinamideHCID 178456054HCID 178456054、化合物

生成物 1

HCID 860853424,4,4-Trifluoro-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-butan-1-one収率 80.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

N-Methoxy-N-methyl-6-(4-trifluoromethyl-phenyl)-nicotinamide (2.0 g, 6.45 mmol) is suspended in anhydrous tetrahydrofuran (25.0 mL), and cooled to 0° C. with stirring under nitrogen. 1,1,1-Trifluoro-butyl magnesium bromide (11.3 mL, 1.14M in tetrahydrofuran, 12.9 mmol) is slowly added to the reaction over 1 h. The reaction is allowed to warm slowly to room temperature and monitored by TLC. Upon complete consumption of starting material, the reaction is carefully acidified with 1N hydrochloric acid, extracted with diethyl ether, washed, dried, and concentrated. The 4,4,4-Trifluoro-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-butan-1-one (1.80 g, 5.19 mmol) 80% yield, is used without further purification.

後処理

  1. temperatureto warm slowly to room temperature
  2. customUpon complete consumption of starting material
  3. extractionextracted with diethyl ether
  4. washwashed
  5. customdried
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-6362fe5d99a04a9caa8135b5e23f2cb7
出典データセット
uspto-grants-2011_08
特許番号
US07989457B2

反応ノート

読み込み中…