4-bromo-N-methoxy-N,1-dimethyl-1H-pyrazole-3-carboxamide → (4-bromo-1-methyl-1H-pyrazol-3-yl)(4-chlorophenyl)methanone

HRID 1772380ノート

反応式

HRID 1772380 の反応式
[Br:1][C:2]1[C:3]([C:8](N(OC)C)=[O:9])=[N:4][N:5]([CH3:7])[CH:6]=1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([Mg]Br)=[CH:17][CH:16]=1>O1CCCC1>[Br:1][C:2]1[C:3]([C:8]([C:18]2[CH:19]=[CH:20][C:15]([Cl:14])=[CH:16][CH:17]=2)=[O:9])=[N:4][N:5]([CH3:7])[CH:6]=1

参加物

4

反応物 2

HCID 866667294-bromo-N-methoxy-N,1-dimethyl-1H-pyrazole-3-carboxamideHCID 178478191HCID 178478191、化合物

生成物 1

HCID 67818210(4-bromo-1-methyl-1H-pyrazol-3-yl)(4-chlorophenyl)methanone収率 84%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of compound 4-bromo-N-methoxy-N,1-dimethyl-1H-pyrazole-3-carboxamide (1.0 g, 4 mmol) in anhydrous tetrahydrofuran (20 mL) under nitrogen atmosphere was added (4-chlorophenyl)magnesium bromide (8 mL) in tetrahydrofuran (1 M) at 0° C., The resulting mixture was stirred for 2 h at room temperature. The reaction was quenched by saturated solution of ammonium chloride, and dichloromethane (100 mL) was added, the separated organic layer was dried over anhydrous sodium sulfate and concentrated in vacuum. The residue was purified by flash chromatography eluting with petroleum ether/ethyl acetate=5:1 to give the titled product as a white solid (1.0 g, 84%). LC/MS m/z 298 [M+H]+; 1H NMR (300 MHz, CDCl3) δ 8.10 (d, J=9 Hz, 2H), 7.53 (s, 1H), 7.43 (d, J=9 Hz, 2H), 3.99 (s, 3H).

後処理

  1. customThe reaction was quenched by saturated solution of ammonium chloride, and dichloromethane (100 mL)
  2. additionwas added
  3. dry with materialthe separated organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by flash chromatography
  6. washeluting with petroleum ether/ethyl acetate=5:1

出典と根拠

ORDレコード
ord-c702549608774c1c817562bf04920c6e
出典データセット
uspto-grants-2016_02
特許番号
US09249161B2

反応ノート

読み込み中…