Hexane → HCID 86661834, compound

HRID 1042131Notes

Reaction equation

HRID 1042131 reaction equation
[CH3:1][S:2]([C:5]1[N:10]=[CH:9][C:8]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16]([C:21]([NH2:23])=O)=[CH:15]3)=[CH:7][CH:6]=1)(=[O:4])=[O:3].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=CC=1.C(OCC)(=O)C.CCCCCC>O1CCCC1>[CH3:1][S:2]([C:5]1[N:10]=[CH:9][C:8]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16]([C:21](=[S:33])[NH2:23])=[CH:15]3)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 87949Lawesson's reagentHCID 66726191HCID 66726191, compound

Product 1

HCID 86661834HCID 86661834, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxamide (4.5 g) in tetrahydrofuran (100 mL) was added a Lawesson's reagent (6 g), and the mixture was stirred with heating under reflux for 1 hr. The reaction mixture was cooled, and concentrated under reduced pressure. The obtained crude product was subjected to basic silica gel column chromatography (ethyl acetate:hexane=0:100 to 100:0, volume ratio) to give the title compound (3.7 g, yield 78%) as yellow powder.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 1 hr
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained crude product

Sources & evidence

ORD record
ord-61879c17abeb43918fc0064465e464c5
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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