(2E)-3-(dimethylamino)-1-(4-methylphenyl)prop-2-en-1-one → 2-[5-(4-Methylphenyl)-1H-pyrazol-1-yl]pyridine-4-carbonitrile

HRID 514340ノート

反応式

HRID 514340 の反応式
Cl.[NH:2]([C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][N:5]=1)[NH2:3].CN(C)/[CH:14]=[CH:15]/[C:16]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)=O>COCCO>[CH3:24][C:21]1[CH:22]=[CH:23][C:18]([C:16]2[N:2]([C:4]3[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][N:5]=3)[N:3]=[CH:14][CH:15]=2)=[CH:19][CH:20]=1

参加物

4

反応物 2

HCID 5398494(2E)-3-(dimethylamino)-1-(4-methylphenyl)prop-2-en-1-oneHCID 867254842-Hydrazinylpyridine-4-carbonitrile hydrochloride salt

生成物 1

HCID 867254852-[5-(4-Methylphenyl)-1H-pyrazol-1-yl]pyridine-4-carbonitrile収率 92.2%

試薬・触媒・溶媒 1

HCID 80192-Methoxyethanol溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-hydrazinylpyridine-4-carbonitrile hydrochloride salt (124 mg, 0.6 mmol, PREPARATION 3) and (2E)-3-(dimethylamino)-1-(4-methylphenyl)prop-2-en-1-one (95 mg, 0.5 mmol) in 2-methoxyethanol (3 mL) was stirred at 100° C. for 2 h. The reaction mixture was cooled, concentrated, and dissolved in EtOAc and then washed with water and brine. The organic phase was dried, concentrated, triturated with EA/PE (1:10, 5 mL), filtered, and dried to give the title compound (120 mg, 92%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 2.38 (3H, s), 6.49 (1H, d, J=1.6 Hz), 7.16 (4H, s), 7.38 (1H, dd, J=5.2, 1.2 Hz), 7.76 (1H, d, J=1.2 Hz), 7.90 (1H, s), 8.44 (1H, d, J=5.2 Hz).

後処理

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. dissolutiondissolved in EtOAc
  4. washwashed with water and brine
  5. customThe organic phase was dried
  6. concentrationconcentrated
  7. customtriturated with EA/PE (1:10, 5 mL)
  8. filtrationfiltered
  9. customdried

出典と根拠

ORDレコード
ord-397cb92814b84e37a09425fcaf3d0664
出典データセット
uspto-grants-2015_08
特許番号
US09107916B2

反応ノート

読み込み中…