32989-56-3Relevant articles and documents
CuH-Catalyzed Enantioselective Alkylation of Indole Derivatives with Ligand-Controlled Regiodivergence
Ye, Yuxuan,Kim, Seoung-Tae,Jeong, Jinhoon,Baik, Mu-Hyun,Buchwald, Stephen L.
supporting information, p. 3901 - 3909 (2019/03/12)
Enantioenriched molecules bearing indole-substituted stereocenters form a class of privileged compounds in biological, medicinal, and organic chemistry. Thus, the development of methods for asymmetric indole alkylation is highly valuable in organic synthesis. Traditionally, achieving N-selectivity in indole alkylation reactions is a significant challenge, since there is an intrinsic preference for alkylation at C3, the most nucleophilic position. Furthermore, selective and predictable access to either N- or C3-alkylated chiral indoles using catalyst control has been a long-standing goal in indole functionalization. Herein, we report a ligand-controlled regiodivergent synthesis of N- and C3-alkylated chiral indoles that relies on a polarity reversal strategy. In contrast to conventional alkylation reactions in which indoles are employed as nucleophiles, this transformation employs electrophilic indole derivatives, N-(benzoyloxy)indoles, as coupling partners. N- or C3-alkylated indoles are prepared with high levels of regio- and enantioselectivity using a copper hydride catalyst. The regioselectivity is governed by the use of either DTBM-SEGPHOS or Ph-BPE as the supporting ligand. Density functional theory (DFT) calculations are conducted to elucidate the origin of the ligand-controlled regiodivergence.
Preparation method of impurity isomer key intermediate of anti-depressive drug
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Paragraph 0018; 0030, (2018/09/11)
The invention relates to a preparation method of an impurity isomer key intermediate of an anti-depressive drug. The preparation method comprises the following steps: (a) mixing sodium periodate, water and DMF (Dimethylformamide); (b) pouring in ice water, adjusting pH with an alkaline solution, extracting by layers, purifying to obtain a compound 4, and performing column chromatography isolationafter reacting at 120 to 150 DEG C to obtain a compound 5; (c) adding the compound 3 and the compound 5 into 1,2-dimethoxyethane, adding sodium hydride under the condition of ice water bath, heating to 40 to 60 DEG C for reacting for 20 to 40 minutes, and heating and refluxing; (d) mixing the compound 6 with a rhodium carbon catalyst, morpholine, methanol and ethanol, reacting under a hydrogen atmosphere, and performing suction filtration and spin drying on filtrate to obtain a compound 7; (e) mixing the compound 7 with formic acid and sodium formate, and heating to 100 to 120 DEG C for refluxreaction; (f) adding anhydrous K2CO3,Cu powder and CuBr, performing reaction under the protection of insert gas at the temperature of 150 to 180 DEG C to obtain a compound 9; cooling to 30 to 60 DEGC, adding NaOH solution to perform reaction, filtering, and purfying to obtain a compound 10.. By adopting the preparation method, a high-purity impurity isomer of the anti-depressive drug can be obtained for accurate control of impurities.
ALPHA 7 NICOTINIC ACETYLCHOLINE ALLOSTERIC MODULATORS, THEIR DERIVATIVES AND USES THEREOF
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Page/Page column 47, (2013/12/03)
The present application is related to compounds represented by Formula I, which are novel positive allosteric modulators of al nAChRs. The application also discloses the treatment of disorders that are responsive to enhancement of acetylcholine action on al nAChRs in a mammal by administering an effective amount of a compound of Formula I.
