Water → [5-(3,5-Dichlorophenyl)sulfanyl-1-isopropyl-4-(4-pyridylmethyl)pyrazol-3-yl]methanol

HRID 1862460ノート

反応式

HRID 1862460 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[C:16]([CH2:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[C:15]([S:24][C:25]2[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=2)[N:14]([CH:33]([CH3:35])[CH3:34])[N:13]=1)=O)C.O.[OH-].[Na+]>O1CCCC1>[Cl:32][C:27]1[CH:26]=[C:25]([S:24][C:15]2[N:14]([CH:33]([CH3:35])[CH3:34])[N:13]=[C:12]([CH2:10][OH:9])[C:16]=2[CH2:17][C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)[CH:30]=[C:29]([Cl:31])[CH:28]=1

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 693539885-(3,5-Dichloro-phenylsulfanyl)-1-isopropyl-4-pyridin-4-ylmethyl-1H-pyrazole-3-carboxylic acid ethyl ester

生成物 1

HCID 514441[5-(3,5-Dichlorophenyl)sulfanyl-1-isopropyl-4-(4-pyridylmethyl)pyrazol-3-yl]methanol収率 64.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

A solution containing 0.4 ml of lithium aluminium hydride (1M solution in THF) in 2 ml of anhydrous tetrahydrofuran at 0° C. under nitrogen was treated dropwise with a solution of 154 mg of 5-(3,5-Dichloro-phenylsulfanyl)-1-isopropyl-4-pyridin-4-ylmethyl-1H-pyrazole-3-carboxylic acid ethyl ester in 2 ml of anhydrous tetrahydrofuran. The mixture was stirred at 0° C. for 0.5 h then treated with 0.012 ml of water, 0.012 ml of 2N sodium hydroxide solution and then 0.018 ml of water. The mixture was stirred for 0.5 h at 0° C.; the mixture was filtered and then the solvent removed. The residue was purified by flash chromatography on silica gel using dichloromethane/methanol (1:19) for the elution to give 90 mg of 5-(3,5dichlorophenylthio)-1-isopropyl-4-[(4-pyridyl)methyl]-1H -pyrazole-3-methanol as a white gum. Mass spectrum (ESI) m/z 408 [M+H]+. 1H NMR (DMSO) 1.30 (d, 6H), 3.90 (s, 2H), 4.55 (d, 2H), 4.72 (m, 1H), 5.30 (t, 1H), 6.85 (s, 2H), 7.15 (d, 2H), 7.35 (s, 1H), 8.30 (d, 2H).

後処理

  1. stirringThe mixture was stirred for 0.5 h at 0° C.
  2. filtrationthe mixture was filtered
  3. customthe solvent removed
  4. customThe residue was purified by flash chromatography on silica gel
  5. washfor the elution

出典と根拠

ORDレコード
ord-e14263741d104f8487ad4a0af3c6b378
出典データセット
uspto-grants-2003_03
特許番号
US06538015B1

反応ノート

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