Lawesson's reagent → HCID 69016906, compound

HRID 1854467Notes

Reaction equation

HRID 1854467 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8](C)[CH:7]=[C:6]2[C:13]1[N:25]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[C:16]2=[N:17][CH:18]=[C:19]([CH2:21][NH:22][CH:23]=O)[N:20]=[C:15]2[CH:14]=1.[CH3:34]OC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1>O1CCOCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1([CH3:34])[CH:11]=[CH:10][C:9]2[C:5]([C:6]([C:13]3[N:25]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:31])[CH3:32])[C:16]4[N:17]=[CH:18][C:19]5[N:20]([CH:23]=[N:22][CH:21]=5)[C:15]=4[CH:14]=3)=[CH:7][N:8]=2)=[CH:4]1

Participants

5

Reactant 2

HCID 87949Lawesson's reagentHCID 58010272HCID 58010272, compound

Product 1

HCID 69016906HCID 69016906, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

N-((6-(5-Methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)formamide (0.10 g, 0.22 mmol) in 1,4-dioxane (4 mL) was treated with Lawesson's Reagent (0.053 g, 0.13 mmol) and heated to about 80° C. in an oil bath for about 15 min. The mixture was cooled and mercuric acetate (0.073 g, 0.23 mmol, Fluka) was added. The mixture was stirred for about 30 min at ambient temperature and another portion of mercuric acetate (0.073 g, 0.228 mmol, Fluka) was added and stirring was continued for about 2 h at ambient temperature. The mixture was diluted with EtOAc (20 mL) and filtered. The solvent was evaporated under reduced pressure then the material was purified by silica gel chromatography eluting with DCM/MeOH (95:5). The material obtained after concentration of the product-containing fractions was further purified by silica gel chromatography eluting with EtOAc to give 7-(5-methoxy-5-methyl-5H-indol-3-yl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.048 g, 49%): LC/MS (Table 2, Method a) Rt=3.16 min; MS m/z: 448 (M+H)+.

Workup

  1. temperatureThe mixture was cooled
  2. stirringstirring
  3. waitwas continued for about 2 h at ambient temperature
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customthe material was purified by silica gel chromatography
  7. washeluting with DCM/MeOH (95:5)
  8. customThe material obtained after concentration of the product-containing fractions
  9. customwas further purified by silica gel chromatography
  10. washeluting with EtOAc

Sources & evidence

ORD record
ord-8f66db087bde42cb94f99959dce09f72
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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