Tetrahydrofuran → HCID 58081030, compound

HRID 1042198Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

To a mixed solution of 7-methyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carbothioamide (2.6 g), ethyl 2-butynoate (1.7 mL), tetrahydrofuran (40 mL), and toluene (60 mL) was added tri-n-butylphosphine (2.2 mL) under an argon atmosphere at room temperature, and the mixture was stirred at 40° C. for 2.5 hr. The reaction solution was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=40:60 to 65:35, volume ratio) to give the title compound (2.59 g, yield 76%) as a pale-yellow amorphous solid.

Workup

concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record: ord-6fae6e65e40240ecb20d7fc3654c296c
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557805B2

Reaction notes

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