Lawesson's reagent → HCID 86002056, compound

HRID 1986053Notes

Reaction equation

HRID 1986053 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=[CH:6][C:5]2=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:28])=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=[CH:6][C:5]2=[S:28]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68888782HCID 68888782, compound

Product 1

HCID 86002056HCID 86002056, compoundYield 138.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture of 6-fluoro-2-pyridin-3-yl-chromen-4-one (128 mg, 0.53 mmol), Lawesson's reagent (129 mg, 0.32 mmol) and anhydrous toluene (3.5 mL) was refluxed under N2 for 0.5 hr. The solvent was removed under vacuum and the residue was purified by silica gel chromatography (EtOAc/MeOH/NEt3, 40/2/1) to give 6-fluoro-2-pyridin-3-yl-chromene-4-thione (114.0 mg, 83.6% yield) as a brown yellow solid which was used in next step without further purification. LC/MS: 258.1 (M+H); LC/Method A/5.94 min, 96.6% purity by area %.

Workup

  1. temperaturewas refluxed under N2 for 0.5 hr
  2. customThe solvent was removed under vacuum
  3. customthe residue was purified by silica gel chromatography (EtOAc/MeOH/NEt3, 40/2/1)

Sources & evidence

ORD record
ord-47d665b8da844a16b0fa86c67e72cb63
Source dataset
uspto-grants-2009_06
Patent number
US07547794B2

Reaction notes

Loading…