ChemicalBook CAS DataBase List (R)-5-BROMO-3-[(1-METHYL-2-PYRROLIDINYL)METHYL]-1H-INDOLE

(R)-5-BROMO-3-[(1-METHYL-2-PYRROLIDINYL)METHYL]-1H-INDOLE synthesis

6synthesis methods

Product Name:(R)-5-BROMO-3-[(1-METHYL-2-PYRROLIDINYL)METHYL]-1H-INDOLE
CAS Number:143322-56-9
Molecular formula:C21H19BrN2O3
Molecular Weight:427.29

10075-50-0 Synthesis

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(R)-N-[(phenylmethoxy)carbonyl]-2-pyrrolidinecarbonyl chloride

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(R)-5-BROMO-3-[(1-METHYL-2-PYRROLIDINYL)METHYL]-1H-INDOLE

143322-56-9
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$125.09/10 mg

Yield:143322-56-9 83%

Reaction Conditions:

Stage #1:5-bromo-1H-indole with aluminum (III) chloride in dichloromethane at 0 - 5; for 1 h;
Stage #2:N-benzyloxycarbonyl-D-proline acid chloride in dichloromethane at 0 - 5; for 6 h;Reagent/catalyst;Concentration;Temperature;Solvent;

Steps:

4 Example 4
5-bromoindole (15.7 g, 80.4 mmol), dichloromethane (140 mL) was added to a 500 ml four-necked flask,The ice bath was cooled to 0 ° C and the aluminum trichloride solid (16.1 g, 120.6 mmol) was slowly added in portions,The internal temperature control in the 0 ~ 5 , stirring reaction 1h, 0 ~ 5 conditions,A solution of N-benzyloxycarbonyl prolyloyl chloride in Example 1 in dichloromethane was added dropwise,The reaction solution was stirred at 0-5 ° C for 6 h. Ice bath, 90mL saturated ammonium chloride solution slowly drip,First filter, the filtrate layer, the organic phase in turn with saturated sodium bicarbonate, saturated salt water washing,After concentration under reduced pressure, the crude product was purified by recrystallization from a mixed solvent of ethyl acetate and n-heptane (1: 1 by volume), vacuum dried at 60 ° C for 8 hours,(R) -3- (N-benzyloxycarbonylpyrrolidin-2-ylcarbonyl) -5-bromo-lH-indole (14.2 g) as a white solid,The yield was 83% and the HPLC purity was 99.2%.

References:

Shanghai Pharmaceutical Industry Research Institute;China Medical Industry Research Institute;Sun, Hui;Zhou, Weicheng;Zhang, Shunli CN104230895, 2017, B Location in patent:Paragraph 0031; 0032; 0033; 0034; 0035; 0036-0044

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144-55-8 Synthesis