2-Methyl-2-butene → 5-[4-(1-hydroxycyclobutyl)phenyl]-6-methyl-1H-indole-3-carboxylic acid

A partial suspension of 5-[4-(1-hydroxycyclobutyl)phenyl]-6-methyl-1H-indole-3-carbaldehyde (130 mg, 0.426 mmol) in tetrahydrofuran (3 mL) and tert-butanol (3 mL) was treated with 2-methyl-2-butene (2.27 mL, 21.4 mmol) followed by a solution of sodium chlorite (538 mg, 6.4 mmol) and sodium phosphate monobasic hydrate (904 mg, 6.5 mmol) in water (2 mL) via glass pipet at room temperature. The reaction mixture was stirred vigorously at room temperature for 62 hours, and was poured into half-diluted saturated aqueous ammonium chloride solution (50 mL). The product was extracted with ethyl acetate (3×60 mL), and the combined organic layers were dried over sodium sulfate, filtered and evaporated. The crude product was purified using reverse-phase chromatography to give the title compound.

1. extractionThe product was extracted with ethyl acetate (3×60 mL)
2. dry with materialthe combined organic layers were dried over sodium sulfate
3. filtrationfiltered
4. customevaporated
5. customThe crude product was purified

ORD 기록

ord-10dc6b922c2c4b17b9229c5202338e88

출처 데이터셋

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09394285B2