Tetrahydrofuran → HCID 68381853, compound

HRID 1188989Notes

Reaction equation

HRID 1188989 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14](=[S:16])[NH2:15])=[CH:10]2)[CH3:3].[C:28]([O:33][CH2:34][CH3:35])(=[O:32])[C:29]#[C:30][CH3:31].C(P(CCCC)CCCC)CCC.O1CCCC1>C1(C)C=CC=CC=1>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:25])=[O:26])=[CH:20][CH:19]=2)[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14]1[S:16][CH:30]([CH2:29][C:28]([O:33][CH2:34][CH3:35])=[O:32])[CH2:31][N:15]=1)=[CH:10]2)[CH3:1]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 13831TributylphosphineHCID 78043Ethyl 2-butynoateHCID 86652838HCID 86652838, compound

Product 1

HCID 68381853HCID 68381853, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 7-(1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carbothioamide (857 mg), ethyl 2-butynoate (0.6 mL), tributylphosphine (0.6 mL), tetrahydrofuran (10 mL) and toluene (15 mL) was stirred at 60° C. for 1.5 h. The mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/99 to 40/60, volume ratio) to give the title compound (381 mg, 41%) as a yellow amorphous solid. MS 517 (MH+).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/99 to 40/60, volume ratio)

Sources & evidence

ORD record
ord-d924aaa95639401b9bf27fe4b2450fb0
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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