2-Chloro-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)nicotinonitrile → 5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(3,4-difluorobenzyl)nicotinonitrile

HRID 916940

反応式

HRID 916940 の反応式
Cl[C:2]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[C:7]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:6][C:3]=1[C:4]#[N:5].[Br-].[F:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:30][Zn+]>C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([C:7]2[C:8]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=3[Cl:17])=[N:9][C:2]([CH2:30][C:29]3[CH:32]=[CH:33][C:34]([F:35])=[C:27]([F:26])[CH:28]=3)=[C:3]([CH:6]=2)[C:4]#[N:5])=[CH:23][CH:22]=1

参加物

5

反応物 2

HCID 101506772-Chloro-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)nicotinonitrileHCID 178505766HCID 178505766、化合物

生成物 1

HCID 102175615-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(3,4-difluorobenzyl)nicotinonitrile

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
50 °C

実験手順

To a dried round bottom flask was added THF (1 mL), the product of Example 36 (0.050 g; 0.127 mmol), 3,4-diflourobenzylzinc bromide (0.27 mL of a 0.5 M solution in THF; 0.134 mmol), and tetrakis(triphenylphosphine) palladium (0) (0.008 g; 5 mol %). The reaction was evacuated and purged with nitrogen several times and stirred at 50° C. for 16 hours. The reaction mixture was cooled to room temperature and diluted with ethyl acetate and washed with saturated aq. NaHCO3 solution (3×), and brine. The organic portion was dried (Na2SO4), filtered, and concentrated in vacuo. Purification done by MPLC (silica gel; 0-10% ethyl acetate/hexane gradient) afforded the desired product: m/e=487 (M+3); Rt=4.8 min.

後処理

  1. customThe reaction was evacuated
  2. custompurged with nitrogen several times
  3. temperatureThe reaction mixture was cooled to room temperature
  4. additiondiluted with ethyl acetate
  5. washwashed with saturated aq. NaHCO3 solution (3×), and brine
  6. dry with materialThe organic portion was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification

出典と根拠

ORDレコード
ord-9e475539642041de812820d7645776ff
出典データセット
uspto-grants-2007_09
特許番号
US07271266B2

関連ノート

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