Dichloromethane → HCID 59136111, compound

HRID 1960527Notes

Reaction equation

HRID 1960527 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>[CH2:30]([O:29][C:24](=[O:28])[CH2:25][CH:26]1[S:14][C:12]([C:9]2[NH:10][C:11]3[C:7]([CH:8]=2)=[CH:6][CH:5]=[CH:4][C:3]=3[N:2]([CH3:1])[S:15]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])=[N:13][CH2:27]1)[CH3:31]

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-b61bf6ae9bf14480b3944c0bb2cd5d5d
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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