Dichloromethane → HCID 59136111, compound

HRID 2239130Notes

Reaction equation

HRID 2239130 reaction equation
[CH3:1][N:2]([S:15]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)(=[O:17])=[O:16])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12](=[S:14])[NH2:13])=[CH:8]2.[C:24]([O:29][CH2:30][CH3:31])(=[O:28])[C:25]#[C:26][CH3:27].C(P(CCCC)CCCC)CCC.ClCCl>O1CCCC1>[CH3:1][N:2]([S:15]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)(=[O:17])=[O:16])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:14][CH:26]([CH2:25][C:24]([O:29][CH2:30][CH3:31])=[O:28])[CH2:27][N:13]=1)=[CH:8]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 13831TributylphosphineHCID 78043Ethyl 2-butynoateHCID 57476153HCID 57476153, compound

Product 1

HCID 59136111HCID 59136111, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-[methyl(pyridin-3-ylsulfonyl)amino]-1H-indole-2-carbothioamide (150 mg), ethyl but-2-ynoate (120 mg), tributylphosphine (90 mg), dichloromethane (20 mL) and tetrahydrofuran (40 mL) was stirred at room temperature for 15 hr, and the mixture was stirred at 50° C. for 3 hr. The reaction mixture was concentrated, and the residue was subjected to basic silica gel column chromatography, and eluted with hexane-ethyl acetate (4:1-1:4, volume ratio). The obtained crystals were further subjected to silica gel column chromatography, and eluted with hexane-ethyl acetate (4:1-1:4, volume ratio) to give pale-yellow crystals. The crystals were recrystallized from ethyl acetate-hexane to give the title compound (60 mg, yield 30%) as pale-yellow prism crystals. melting point 146-147° C.

Workup

  1. stirringthe mixture was stirred at 50° C. for 3 hr
  2. concentrationThe reaction mixture was concentrated
  3. washeluted with hexane-ethyl acetate (4:1-1:4, volume ratio)
  4. washeluted with hexane-ethyl acetate (4:1-1:4, volume ratio)
  5. customto give pale-yellow crystals
  6. customThe crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-12102ecf0322469083cfb60c6b2f4051
Source dataset
uspto-grants-2010_05
Patent number
US07718798B2

Reaction notes

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