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

HRID 2401436ノート

反応式

HRID 2401436 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-c71cac47280541ba980084ca1daa03fb
出典データセット
uspto-grants-2014_08
特許番号
US08796261B2

反応ノート

読み込み中…