Lawesson's reagent → HCID 86652850, compound

HRID 1188962Notes

Reaction equation

HRID 1188962 reaction equation
[F:1][C:2]1[C:10]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[C:9]2[C:5]([CH:6]=[C:7]([C:16]([NH2:18])=O)[NH:8]2)=[CH:4][C:3]=1[O:19][C:20]1[CH:21]=[N:22][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:24][CH:25]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:39])=CC=1>O1CCCC1>[F:1][C:2]1[C:10]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[C:9]2[C:5]([CH:6]=[C:7]([C:16](=[S:39])[NH2:18])[NH:8]2)=[CH:4][C:3]=1[O:19][C:20]1[CH:21]=[N:22][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 66898014HCID 66898014, compound

Product 1

HCID 86652850HCID 86652850, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 6-fluoro-7-(2-methoxyethoxy)-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxamide (0.61 g) and Lawesson's reagent (0.61 g) in tetrahydrofuran (25 mL) was stirred at 55° C. for 2 h. The reaction mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:hexane=40:60 to 70:30, volume ratio) to give light yellow crystals, which were washed with ethyl acetate-hexane to give the title compound (585 mg, 92%) as light yellow crystals. MS 440 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by silica gel chromatography (ethyl acetate:hexane=40:60 to 70:30, volume ratio)
  3. customto give light yellow crystals, which
  4. washwere washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-4ada3b90f97e41c882676c9e255d4380
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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