Lawesson's reagent → 7-Ethoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carbothioamide

HRID 1188966Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([O:16][C:17]2[CH:18]=[N:19][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:21][CH:22]=2)[CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([NH2:15])=O)=[CH:9]2)[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:36])=CC=1>O1CCCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([O:16][C:17]2[CH:18]=[N:19][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:21][CH:22]=2)[CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13](=[S:36])[NH2:15])=[CH:9]2)[CH3:2]

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 7-ethoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxamide (0.43 g) and Lawesson's reagent (0.28 g) in tetrahydrofuran (30 mL) was stirred at 55° C. for 2 h. The reaction mixture was concentrated to give a light yellow oil, which was crystallized from ethyl acetate-hexane to give the title compound (414 mg, 92%) as light yellow crystals. MS 392 (MH+).

Workup

concentrationThe reaction mixture was concentrated
customto give a light yellow oil, which
customwas crystallized from ethyl acetate-hexane

Sources & evidence

ORD record: ord-12a0023fa1c54c75b512ce79cc5234e0
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673942B2

Reaction notes

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