Welcome to chemicalbook!
Chinese English Japanese Germany Korea
010-86108875
Try our best to find the right business for you.
Do not miss inquiry messages Please log in to view all inquiry messages.

Welcome back!

ChemicalBook CAS DataBase List Ethyl 5-Bromoindole-2-carboxylate
16732-70-0

Ethyl 5-Bromoindole-2-carboxylate synthesis

10synthesis methods
The preparation of Ethyl 5-Bromoindole-2-carboxylate was as follows: A 25 mL Schlenk reaction tube was used, and 69 mg of p-bromoaniline, 9 mg of palladium acetate, and 80 mg of molecular sieve were added. Then, 93 mg of ethyl 2-oxopropionate, 96 mg of acetic acid, and 2 mL of dimethyl sulfoxide were injected. A 200 mL oxygen bulb was attached, and the mixture was stirred at 70 °C for 18 hours using a chemical book. After the reaction was complete, 15 mL of ethyl acetate was added to dilute the reaction solution. The mixture was filtered, washed twice with 10 mL of brine, and the organic phase was separated. The aqueous phase was extracted once with ethyl acetate. The organic phases were combined, and column chromatography was used to separate the target product, yielding 50 mg of pure ethyl 5-bromoindole-2-carboxylate (47% yield).
-

Yield:16732-70-0 94%

Reaction Conditions:

with sulfuric acid at 80; for 12 h;

Steps:

20.a a) 5-Bromo-lH-indole-2-carboxylic acid ethyl ester
Example 20 5-(l-Isopropyl-piperidin-4-yl)-lH-indole-2-carboxylic acid (3-fluoro-phenyl)-amide a) 5-Bromo-lH-indole-2-carboxylic acid ethyl ester 5-Bromoindole-2-carboxylic acid (2.5 g; 10.4 mmol) was dissolved in ethanol (100 mL). Concentrated sulphuric acid (2.5 mL) was added and the reaction mixture heated at 80°C for 12 hours. The mixture was cooled to room temperature and the solution neutralized to pH 7 using aqueous sodium bicarbonate solution (50 mL). The reaction mixture was concentrated in vacuo to remove ethanol, and the aqueous phase was extracted using ethyl acetate (2 x 100 mL). The combined organic phases were dried over magnesium sulfate, filtered and concentrated in vacuo to afford the title compound (2.63 g, 94 %). HPLC-MS (purity; retention time) = 100 %; 2.31 min. MS ISP (m/e): 270.0/268.1 (100/100) [(M+H)+]

References:

F. HOFFMANN-LA ROCHE AG;HOFFMANN-LA ROCHE INC.;BAUMANN, Karlheinz;FLOHR, Alexander;JOLIDON, Synese;KNUST, Henner;LUEBBERS, Thomas;NETTEKOVEN, Matthias WO2014/60386, 2014, A1 Location in patent:Page/Page column 43

FullText

Ethyl 5-Bromoindole-2-carboxylate Related Search: