Ethyl Acetate → ethyl{2-[5-{[6-(methoxymethyl)pyridin-3-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate

HRID 1042148Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 5-{[6-(methoxymethyl)pyridin-3-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carbothioamide (1.5 g) in tetrahydrofuran (10 mL) and toluene (15 mL) were added ethyl 2-butynoate (1.02 g) and tri-n-butylphosphine (0.73 g), and the mixture was stirred at 90° C. for 1 hr. The reaction mixture was cooled, and concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (ethyl acetate:hexane=0:100 to 100:0, volume ratio) to give the title compound (1.25 g, yield 66%) as a yellow amorphous solid.

Workup

temperatureThe reaction mixture was cooled
concentrationconcentrated under reduced pressure
customThe obtained crude product

Sources & evidence

ORD record: ord-36478b42b407405cbc65e4fa0cecbe69
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557805B2

Reaction notes

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