Ethyl 2-butynoate → Ethyl (2-{5-[4-(methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetate

温度

50 °C

5-[4-(Methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-indole-2-carboxamide (500 mg) was dissolved in tetrahydrofuran (20 mL), Lawesson's reagent (455 mg) was added, and the mixture was stirred at 50° C. for 1 hr. The reaction solution was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (ethyl acetate:hexane=20:80 to 70:30, volume ratio) to give a yellow oil. The obtained yellow oil was dissolved in a mixed solvent of tetrahydrofuran (10 mL)-toluene (15 mL), ethyl 2-butynoate (0.26 mL) and tributylphosphine (0.30 mL) were added, and the mixture was stirred at 50° 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=10:90 to 100:0, volume ratio) to give the title compound (310 mg, yield 48%) as an orange oil. MS 573 (MH+).

1. concentrationThe reaction solution was concentrated under reduced pressure
2. customto give a yellow oil
3. additionwere added
4. stirringthe mixture was stirred at 50° C. for 2.5 hr
5. concentrationThe reaction solution was concentrated under reduced pressure

ORDレコード

ord-15f0df746ce9425680ee5c0d4b56b74c

出典データセット

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08673942B2