Tetrahydrofuran → HCID 58236985, compound

HRID 1189048Notes

Reaction equation

HRID 1189048 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12](=[S:14])[NH2:13])=[CH:8]2.[C:26]([O:31][CH2:32][CH3:33])(=[O:30])[C:27]#[C:28][CH3:29].O1CCCC1.C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:14][CH:28]([CH2:27][C:26]([O:31][CH2:32][CH3:33])=[O:30])[CH2:29][N:13]=1)=[CH:8]2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 13831Tributylphosphine2×HCID 78043Ethyl 2-butynoate2×HCID 58236986HCID 58236986, compound

Product 1

HCID 58236985HCID 58236985, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of 7-methoxy-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carbothioamide (0.69 g), ethyl 2-butynoate (0.43 mL), tetrahydrofuran (15 mL) and toluene (25 mL) was added tributylphosphine (0.54 mL) at room temperature under argon atmosphere. After the mixture was stirred at 40° C. for 4 h, ethyl 2-butynoate (0.22 mL) and tributylphosphine (0.27 mL) were added thereto. After stirring at 40° C. for 2 h, the reaction mixture was concentrated to give a light brown oil, which was purified by silica gel chromatography (ethyl acetate:hexane=30:70 to 75:25, volume ratio) to give the title compound (684 mg, 72%) as a light yellow oil. MS 489 (MH+).

Workup

  1. stirringAfter stirring at 40° C. for 2 h
  2. concentrationthe reaction mixture was concentrated
  3. customto give a light brown oil, which
  4. customwas purified by silica gel chromatography (ethyl acetate:hexane=30:70 to 75:25, volume ratio)

Sources & evidence

ORD record
ord-7e91ad4f29d54b5ebfa6446cd8e7b288
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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