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

HRID 1042104Notes

Reaction equation

HRID 1042104 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[C:18]([O:20][CH:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[CH:19]=2)[NH:16][C:15]([C:27]([NH2:29])=O)=[CH:14]3)=[CH:6][CH:5]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:39])=CC=1.C(OCC)(=O)C.CCCCCC>O1CCCC1>[CH3:1][O:2][CH2:3][C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[C:18]([O:20][CH:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[CH:19]=2)[NH:16][C:15]([C:27](=[S:39])[NH2:29])=[CH:14]3)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 87949Lawesson's reagentHCID 66726164HCID 66726164, compound

Product 1

HCID 866618245-{[6-(Methoxymethyl)pyridin-3-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carbothioamideYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-{[6-(methoxymethyl)pyridin-3-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carboxamide (1.45 g) in tetrahydrofuran (20 mL) was added a Lawesson's reagent (1.6 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 silica gel column chromatography (ethyl acetate:hexane=0:100 to 100:0, volume ratio) to give the title compound (1.5 g, yield 99%) 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-4c216918182343919a12e21640dcf83f
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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