Tetrahydrofuran → HCID 70963860, compound

HRID 1189038Notes

Reaction equation

HRID 1189038 reaction equation
[F:1][C:2]1[C:10]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[C:9]2[C:5]([CH:6]=[C:7]([C:16](=[S:18])[NH2:17])[NH:8]2)=[CH:4][C:3]=1[O:19][C:20]1[CH:21]=[N:22][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:24][CH:25]=1.[C:30]([O:35][CH2:36][CH3:37])(=[O:34])[C:31]#[C:32][CH3:33].O1CCCC1.C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[F:1][C:2]1[C:10]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[C:9]2[C:5]([CH:6]=[C:7]([C:16]3[S:18][CH:32]([CH2:31][C:30]([O:35][CH2:36][CH3:37])=[O:34])[CH2:33][N:17]=3)[NH:8]2)=[CH:4][C:3]=1[O:19][C:20]1[CH:21]=[N:22][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 13831TributylphosphineHCID 78043Ethyl 2-butynoateHCID 86652850HCID 86652850, compound

Product 1

HCID 70963860HCID 70963860, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of 6-fluoro-7-(2-methoxyethoxy)-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carbothioamide (0.58 g), ethyl 2-butynoate (0.31 mL), tetrahydrofuran (10 mL) and toluene (15 mL) was added tributylphosphine (0.40 mL) at room temperature under argon atmosphere. After stirring at 40° C. for 3 h, the reaction mixture was concentrated to give a light brown oil, which was purified by silica gel chromatography (ethyl acetate:hexane=35:65 to 100:0, volume ratio) to give the title compound (525 mg, 72%) as a pale yellow oil. MS 552 (MH+).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customto give a light brown oil, which
  3. customwas purified by silica gel chromatography (ethyl acetate:hexane=35:65 to 100:0, volume ratio)

Sources & evidence

ORD record
ord-6d3034f2bd0a4d6b80397780cdf4ee21
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

Loading…