Lawesson's reagent → 6-Pyridin-3-yl-3,4-dihydroquinoline-2(1H)-thione

HRID 1521571Notes

Reaction equation

HRID 1521571 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=O)[CH2:11][CH2:10]3)[CH:2]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:27]2)=CC=1>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=[S:27])[CH2:11][CH2:10]3)[CH:2]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 137288626-(Pyridin-3-yl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 251803006-Pyridin-3-yl-3,4-dihydroquinoline-2(1H)-thione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To the title compound from Example 1 Step A (200 mg, 0.892 mmol) and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide (180 mg, 0.446 mmol) was added toluene (1.8 mL). The suspension was heated to reflux for 45 minutes. The reaction was then cooled to room temperature and concentrated under reduced pressure. Purification by flash chromatography on silica gel (0-15% methanol in ethyl acetate) provided the title compound: LCMS m/z 241.22 [M+H]+; 1H NMR (500 MHz, CD3OD) δ 8.86 (d, J=2.0 Hz, 1H), 8.55 (dd, J=1.5, 4.8 Hz, 1H), 8.11 (ddd, J=1.9, 2.2, 8.2 Hz, 1H), 7.61-7.58 (m, 2H), 7.53 (dd, J=4.9, 8.0 Hz, 1H), 7.20 (d, J=8.1 Hz, 1H), 3.09-3.06 (m, 2H), 2.99-2.96 (m, 2H).

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux for 45 minutes
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash chromatography on silica gel (0-15% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-9f75bb5134034467983e74feb3c1c5a7
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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