Hexane → 5-{[6-(Methylsulfonyl)pyridin-3-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carbothioamide

HRID 1042126Notes

Reaction equation

HRID 1042126 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](=[C:19]([O:21][CH:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:20]=2)[NH:17][C:16]([C:28]([NH2:30])=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:40])=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](=[C:19]([O:21][CH:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:20]=2)[NH:17][C:16]([C:28](=[S:40])[NH2:30])=[CH:15]3)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 87949Lawesson's reagentHCID 667260845-{[6-(Methylsulfonyl)pyridin-3-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carboxamide

Product 1

HCID 866618325-{[6-(Methylsulfonyl)pyridin-3-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carbothioamideYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carboxamide (1.35 g) in tetrahydrofuran (20 mL) was added a Lawesson's reagent (1.4 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 silica gel column chromatography (ethyl acetate:hexane=0:100 to 100:0, volume ratio) to give the title compound (1.4 g, yield 100%) as a yellow amorphous solid.

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-ccf3e2fab4a042bd83170c16fd9f332b
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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