Lawesson's reagent → HCID 86634860, compound

HRID 1851602Notes

Reaction equation

[CH2:1]([N:3]([S:18]([C:21]1[S:22][CH:23]=[CH:24][CH:25]=1)(=[O:20])=[O:19])[C:4]1[CH:5]=[C:6]([CH3:17])[C:7]([CH3:16])=[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:35])=CC=1>O1CCCC1>[CH2:1]([N:3]([S:18]([C:21]1[S:22][CH:23]=[CH:24][CH:25]=1)(=[O:20])=[O:19])[C:4]1[CH:5]=[C:6]([CH3:17])[C:7]([CH3:16])=[C:8]2[C:12]=1[NH:11][C:10]([C:13](=[S:35])[NH2:15])=[CH:9]2)[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 7-[ethyl(2-thienylsulfonyl)amino]-4,5-dimethyl-1H-indole-2-carboxamide (0.20 g), Lawesson's reagent (0.22 g) and tetrahydrofuran (10 mL) was stirred at 40° C. for 5 hr. The reaction solution was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography(ethyl acetate:hexane=1:9-ethyl acetate) to give 7-[ethyl(2-thienylsulfonyl)amino]-4,5-dimethyl-1H-indole-2-carbothioamide (0.16 g, yield 77%) as pale-yellow crystals. A mixed solution of the obtained crystals (0.16 g), bromomalonaldehyde (0.13 g) and N,N-dimethylacetamide (8 mL) was stirred at 80° C. for 3 hr. The reaction solution was diluted with ethyl acetate, washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:9-1:3) to give the title compound (85 mg, yield 47%) as pale-yellow crystals.

Workup

concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record: ord-93f0ecfc76624f6eab57bc5178fe5d0d
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957070B2

Reaction notes

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