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

HRID 2169770노트

반응식

HRID 2169770 반응식
[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

참가 물질

6

반응물 3

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

생성물 2

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-95fc3aeb00d448bfb20decca2494f5f9
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09049864B2

반응 노트

불러오는 중…