Tetrahydrofuran → Ethyl [2-(7-ethoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetate

HRID 1189043Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

To a stirred solution of 7-ethoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carbothioamide (0.41 g), ethyl 2-butynoate (0.25 mL), tetrahydrofuran (10 mL) and toluene (15 mL) was added tributylphosphine (0.31 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=30:70 to 50:50, volume ratio) to give the title compound (350 mg, 66%) as a light yellow oil. MS 504 (MH+).

Workup

concentrationthe reaction mixture was concentrated
customto give a light brown oil, which
customwas purified by silica gel chromatography (ethyl acetate:hexane=30:70 to 50:50, volume ratio)

Sources & evidence

ORD record: ord-b78ece6f69814d67af3839266f994c05
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673942B2

Reaction notes

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