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

HRID 2169770Notes

Reaction equation

HRID 2169770 reaction equation
[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

Participants

6

Reactant 3

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

Product 2

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-95fc3aeb00d448bfb20decca2494f5f9
Source dataset
uspto-grants-2015_06
Patent number
US09049864B2

Reaction notes

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