Lawesson's reagent → HCID 78108198, compound

HRID 1056662Notes

Reaction equation

HRID 1056662 reaction equation
[CH3:1][CH2:2][O:3][C:4]1[C:9]([CH:10]2[C:20]3[C:15](=[CH:16][C:17]4[O:23][CH2:22][O:21][C:18]=4[CH:19]=3)[NH:14][C:12](=O)[CH2:11]2)=[CH:8][CH:7]=[CH:6][CH:5]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=CC=1>C1(C)C=CC=CC=1>[CH2:2]([O:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=1[CH:10]1[C:20]2[CH:19]=[C:18]3[O:21][CH2:22][O:23][C:17]3=[CH:16][C:15]=2[NH:14][C:12](=[S:33])[CH2:11]1)[CH3:1]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 6563468-(2-Ethoxyphenyl)-7,8-dihydro-1,3-Dioxolo[4,5-g]quinolin-6(5H)-one

Product 1

HCID 78108198HCID 78108198, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

FQI-1 (200 mg, 1.0 equiv) was weighed into a dry reaction vial under an atmosphere of nitrogen. Dry toluene (4.3 mL) was added, followed by Lawesson's reagent (416 mg, 1.6 equiv). The vial was tightly sealed and the reaction was heated to reflux overnight. After cooling, the solvent was removed in vacuo and the residue was purified by flash column chromatography (gradient of 20% to 70% ethyl acetate in hexanes). Fractions which contained product were pooled to give 120 mg of an impure red oil which was recrystallized from dichloromethane/hexanes to give Compound X as white needles (40 mg, 19%). 1H NMR (400 MHz, CDCl3) δ=9.69 (br. s., 1 H), 7.20 (ddd, J=2.9, 6.0, 8.3 Hz, 1 H), 6.89-6.82 (m, 3 H), 6.46 (d, J=3.1 Hz, 2 H), 5.93 (d, J=1.2 Hz, 2 H), 4.54 (dd, J=6.4, 7.8 Hz, 1 H), 4.10-4.02 (m, 2 H), 3.42 (dd, J=7.8, 17.0 Hz, 1H), 3.23 (dd, J=6.4, 17.0 Hz, 1 H), 1.40 (t, J=7.0 Hz, 3 H). ESI-MS (M+H+) m/z=328.

Workup

  1. customThe vial was tightly sealed
  2. temperaturethe reaction was heated
  3. temperatureto reflux overnight
  4. temperatureAfter cooling
  5. customthe solvent was removed in vacuo
  6. customthe residue was purified by flash column chromatography (gradient of 20% to 70% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-358604dfc457474799f7cf2e544ffc30
Source dataset
uspto-grants-2016_07
Patent number
US09399644B2

Reaction notes

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