HCID 21090548、化合物 → 4-[[5-(3,5-Dichlorophenyl)sulfanyl-1-isopropyl-3-methyl-pyrazol-4-yl]methyl]pyridine

HRID 350882ノート

反応式

HRID 350882 の反応式
[P](I)(I)(I)I.[Cl:6][C:7]1[CH:8]=[C:9]([S:14][C:15]2[N:19]([CH:20]([CH3:22])[CH3:21])[N:18]=[C:17]([CH3:23])[C:16]=2[C:24]2C=CN=C(C)[C:25]=2O)[CH:10]=[C:11]([Cl:13])[CH:12]=1.S(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[Cl:6][C:7]1[CH:8]=[C:9]([S:14][C:15]2[N:19]([CH:20]([CH3:21])[CH3:22])[N:18]=[C:17]([CH3:23])[C:16]=2[CH2:24][C:25]2[CH:21]=[CH:20][N:19]=[CH:15][CH:16]=2)[CH:10]=[C:11]([Cl:13])[CH:12]=1

参加物

5

反応物 3

HCID 21090548HCID 21090548、化合物HCID 23665763Sodium BisulfiteHCID 178506614HCID 178506614、化合物

生成物 1

HCID 99085114-[[5-(3,5-Dichlorophenyl)sulfanyl-1-isopropyl-3-methyl-pyrazol-4-yl]methyl]pyridine

試薬・触媒・溶媒 1

HCID 241Benzene溶媒2 回

反応条件

温度
80 °C

実験手順

A solution of 466 mg of phosphorus tetraiodide in 15 mL of benzene was heated at 80° C. for 15 minutes. To this solution was added dropwise a solution of 400 mg of 4-[[5-(3,5-dichloro-phenylsulfanyl)-1-isopropyl-3-methyl-1H-pyrazol-4-yl]-hydroxy-methyl-pyridine in 10 mL of benzene. The mixture was then heated at 80° C. for 1 hour then allowed to cool to room temperature. Then 8 mL of 10% aqueous sodium bisulphite solution was added and the biphasic mixture stirred for 1 hour. The aqueous phase was extracted three times with 30 mL of ethyl acetate and combined extracts were washed with brine, dried, filtered and evaporated to give a yellow residue which was purified by flash chromatography on silica gel using ethyl acetate/hexane (1:1 then 2:1) for the elution to give 238 mg of 4-[5-(3,5-dichloro-phenylsulfanyl)-1-isopropyl-3-methyl-1H-pyrazol-4-ylmethyl]-pyridine as a white solid. Mass spectrum (ES) m/z 392 [M+H]+, 433 [M+H+MeCN]+.

後処理

  1. temperatureto cool to room temperature
  2. extractionThe aqueous phase was extracted three times with 30 mL of ethyl acetate
  3. washwere washed with brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customto give a yellow residue which
  8. customwas purified by flash chromatography on silica gel
  9. wash2:1) for the elution

出典と根拠

ORDレコード
ord-90e498629e504fe0a54ccfd8b36e363c
出典データセット
uspto-grants-2007_02
特許番号
US07183296B2

反応ノート

読み込み中…