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

HRID 1042169Notes

Reaction equation

[CH3:1][S:2]([C:5]1[N:10]=[CH:9][C:8]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[C:19]([O:21][CH:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:20]=2)[NH:17][C:16]([C:28](=[S:30])[NH2:29])=[CH:15]3)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:31]([O:36][CH2:37][CH3:38])(=[O:35])[C:32]#[C:33][CH3:34].C(P(CCCC)CCCC)CCC.C(OCC)(=O)C>O1CCCC1.C1(C)C=CC=CC=1.CCCCCC>[CH2:37]([O:36][C:31](=[O:35])[CH2:32][CH:33]1[S:30][C:28]([C:16]2[NH:17][C:18]3[C:14]([CH:15]=2)=[CH:13][C:12]([O:11][C:8]2[CH:9]=[N:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=2)=[CH:20][C:19]=3[O:21][CH:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)=[N:29][CH2:34]1)[CH3:38]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carbothioamide (1.4 g) in tetrahydrofuran (10 mL) and toluene (15 mL) were added ethyl 2-butynoate (0.88 g) and tri-n-butylphosphine (0.63 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 (1.05 g, yield 60%) as a yellow amorphous solid.

Workup

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

Sources & evidence

ORD record: ord-50657130d46348119b49421affe89f7d
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557805B2

Reaction notes

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