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

HRID 1772380노트

반응식

HRID 1772380 반응식
[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

참가 물질

4

반응물 2

HCID 866667294-bromo-N-methoxy-N,1-dimethyl-1H-pyrazole-3-carboxamideHCID 178478191HCID 178478191, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c702549608774c1c817562bf04920c6e
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249161B2

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