Triethylamine → [5-(2,3-Dichloroindol-1-yl)-1,3-dimethyl-6-oxo-pyridazin-4-yl]isopropylsulfanylformate

HRID 2169770ノート

反応式

HRID 2169770 の反応式
[Cl:1][C:2]1[N:3]([CH:12]2[C:17](=[O:18])[C:16]([CH3:19])=[N:15][N:14]([CH3:20])[C:13]2=[O:21])[C:4]2[C:9]([C:10]=1[Cl:11])=[CH:8][CH:7]=[CH:6][CH:5]=2.C(N([CH2:27][CH3:28])CC)C.Cl[C:30]([S:32][CH:33]([CH3:35])[CH3:34])=[O:31]>ClCCl>[CH3:28][CH2:27][O:31][C:17]([CH3:12])=[O:18].[CH3:6][CH2:5][CH2:4][CH:9]([CH3:10])[CH3:8].[Cl:1][C:2]1[N:3]([C:12]2[C:13](=[O:21])[N:14]([CH3:20])[N:15]=[C:16]([CH3:19])[C:17]=2[O:18][C:30]([S:32][CH:33]([CH3:35])[CH3:34])=[O:31])[C:4]2[C:9]([C:10]=1[Cl:11])=[CH:8][CH:7]=[CH:6][CH:5]=2

参加物

6

反応物 3

HCID 8471TriethylamineHCID 13279441S-Isopropyl chlorothioformateHCID 898762134-(2,3-Dichloroindol-1-yl)-2,6-dimethyl-pyridazine-3,5-dione

生成物 2

HCID 21882781Isohexane ethyl acetate収率 0%HCID 89876363[5-(2,3-Dichloroindol-1-yl)-1,3-dimethyl-6-oxo-pyridazin-4-yl]isopropylsulfanylformate収率 177.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred suspension of 4-(2,3-dichloroindol-1-yl)-2,6-dimethyl-pyridazine-3,5-dione (120 mg, 0.370 mmol) in dichloromethane (8 mL) at RT is added triethylamine (129 μL, 0.925 mmol). The reaction mixture turned homogeneous. S-Isopropyl chlorothioformate (69 μL, 0.555 mmol) is added and the reaction mixture is stirred for 15 min. The mixture is then quenched with water (10 mL) and the layers are separated. The aqueous layer is re-extracted with dichloromethane (10 mL×3) and the combined organics were dried (phase separator cartridge) and concentrated under reduced pressure onto silica. Flash chromatography (combiflash, 0-20% EtOAc/isohexane) afforded the desired product [5-(2,3-dichloroindol-1-yl)-1,3-dimethyl-6-oxo-pyridazin-4-yl]isopropylsulfanylformate (140 mg, 0.328 mmol, 89%) as yellow solid.

後処理

  1. customThe mixture is then quenched with water (10 mL)
  2. customthe layers are separated
  3. extractionThe aqueous layer is re-extracted with dichloromethane (10 mL×3)
  4. customthe combined organics were dried (phase separator cartridge)
  5. concentrationconcentrated under reduced pressure onto silica

出典と根拠

ORDレコード
ord-95fc3aeb00d448bfb20decca2494f5f9
出典データセット
uspto-grants-2015_06
特許番号
US09049864B2

反応ノート

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