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

Product Name: (R)-5-BROMO-3-[(1-METHYL-2-PYRROLIDINYL)METHYL]-1H-INDOLE
CAS No.: 143322-56-9
Chemical Name: (R)-5-BROMO-3-[(1-METHYL-2-PYRROLIDINYL)METHYL]-1H-INDOLE
Synonyms: InterMediate of Eletriptan;3-(N- benzyloxycarbonyl-D-prolyl)-5-bromoindole;(5R)3-(N-benzyloxycarbonyl-D-prolyl)-5-bromoindole;(R)-5-bromo-3-[(1-methyl-2-pyrrolidinyl)methyl]-1H-indole;(R)-Benzyl 2-(5-bromo-1H-indole-3-carbonyl)-pyrrolidine-1-carboxylate;(R)-(5-bromo-1H-indol-3-yl)[N-[(phenylmethoxy)carbonyl]-2-pyrrolidinyl]methanone;(R)-2-[(5-Bromo-1H-indol-3-yl)carbonyl]-1-pyrrolidinecarboxylic acid benzyl ester;(2R)-2-[(5-BroMo-1H-indol-3-yl)carbonyl]-1-pyrrolidinecarboxylic Acid PhenylMethyl Ester;1-Pyrrolidinecarboxylic acid, 2-[(5-bromo-1H-indol-3-yl)carbonyl]-, phenylmethyl ester, (R)-;1-Pyrrolidinecarboxylic acid, 2-[(5-bromo-1H-indol-3-yl)carbonyl]-, phenylmethyl ester, (2R)-
CBNumber: CB32129544
Molecular Formula: C21H19BrN2O3
Formula Weight: 427.29
MOL File: 143322-56-9.mol

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

Boiling point:: 605.0±55.0 °C(Predicted)
Density: 1.505
storage temp.: 2-8°C
solubility: soluble in Dichloromethanol, Ethyl Acetate, Methanol
form: Solid
pka: 14.40±0.30(Predicted)
color: White
CAS DataBase Reference: 143322-56-9(CAS DataBase Reference)

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

TRC

Product number: B285927
Product name: R-3-(N-Benzyloxycarbonylpyrrolidin-2-ylcarbonyl)-5-bromo-1H-indole
Packaging: 250mg
Price: $1100
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FB18508
Product name: R-3-(N-Benzyloxycarbonylpyrrolidin-2-ylcarbonyl)-5-bromo-1H-indole
Packaging: 10mg
Price: $125.1
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FB18508
Product name: R-3-(N-Benzyloxycarbonylpyrrolidin-2-ylcarbonyl)-5-bromo-1H-indole
Packaging: 25mg
Price: $227.5
Updated: 2021/12/16

Matrix Scientific

Product number: 096542
Product name: (R)-Benzyl 2-(5-bromo-1H-indole-3-carbonyl)-pyrrolidine-1-carboxylate
Purity: 95+%
Packaging: 250mg
Price: $288
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FB18508
Product name: R-3-(N-Benzyloxycarbonylpyrrolidin-2-ylcarbonyl)-5-bromo-1H-indole
Packaging: 50mg
Price: $413.5
Updated: 2021/12/16

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(R)-5-BROMO-3-[(1-METHYL-2-PYRROLIDINYL)METHYL]-1H-INDOLE Chemical Properties,Usage,Production

Chemical Properties

White Solid

Synthesis

10075-50-0

61350-62-7

143322-56-9

General procedure for the synthesis of benzyl (R)-2-(5-bromo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate from 5-bromoindole and benzyl (R)-2-(chlorocarbonyl)pyrrolidine-1-carboxylate: 5-bromoindole (15.7 g, 80.4 mmol) was added to a 500 mL four-necked flask with dichloromethane (140 mL). The temperature of the reaction system was lowered to 0 °C under cooling in an ice bath, and aluminum trichloride solid (16.1 g, 120.6 mmol) was slowly added, taking care to add it in batches and controlling the internal temperature between 0 and 5 °C. After addition, the reaction was continued to be stirred at 0~5°C for 1 hour. Subsequently, a dichloromethane solution of N-benzyloxycarbonyl prolyl chloride prepared in Example 1 was slowly added dropwise under the same temperature conditions. After the dropwise addition was completed, the reaction was continued to be stirred for 6 hours by keeping 0~5°C. At the end of the reaction, the reaction system was placed in an ice bath and the reaction was quenched by slowly dropping 90 mL of saturated ammonium chloride solution. The reaction mixture was filtered, the filtrate was separated and the organic phase was washed with saturated sodium bicarbonate solution and saturated brine sequentially. After the solvent was removed by concentration under reduced pressure, the resulting crude product was purified by recrystallization using a solvent mixture of ethyl acetate and n-heptane (1:1, v/v). The purified product was dried under vacuum at 60 °C for 8 h to afford (R)-3-(N-benzyloxycarbonylpyrrolidin-2-ylcarbonyl)-5-bromo-1H-indole (14.2 g) as a white solid in 83% yield and 99.2% HPLC purity.

References

[1] Patent: CN104230895, 2017, B. Location in patent: Paragraph 0031; 0032; 0033; 0034; 0035; 0036-0044
[2] Medicinal Chemistry Research, 1999, vol. 9, # 9, p. 668 - 674
[3] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 20, p. 3419 - 3421
[4] Patent: US2008/319205, 2008, A1. Location in patent: Page/Page column 7
[5] Patent: US2011/166364, 2011, A1. Location in patent: Page/Page column 4

(R)-5-BROMO-3-[(1-METHYL-2-PYRROLIDINYL)METHYL]-1H-INDOLE Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from (R)-5-BROMO-3-[(1-METHYL-2-PYRROLIDINYL)METHYL]-1H-INDOLE manufacturers

Career Henan Chemical Co

Product: (R)-5-BROMO-3-[(1-METHYL-2-PYRROLIDINYL)METHYL]-1H-INDOLE 143322-56-9
Price: US $1.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 200kgs
Release date: 2020-01-28

143322-56-9, (R)-5-BROMO-3-[(1-METHYL-2-PYRROLIDINYL)METHYL]-1H-INDOLERelated Search:

Benzo[b]thiophene-2-Methanol, α-(5-broMo-2-fluorophenyl)- Benzyl formate 5-BROMO-N,N-DIMETHYLTRYPTAMINE (5-BROMO-1H-INDOL-3-YL)-((R)-1-METHYL-PYRROLIDIN-2-YL)-METHANONE (R)-2-(5-BROMO-1H-INDOLE-3-CARBONYL)-PYRROLIDINE-1-CARBOXYLIC ACID BENZYL ESTER 5-BROMOTRYPTAMINE HYDROCHLORIDE (R)-5-BROMO-3-[(1-METHYL-2-PYRROLIDINYL)METHYL]-1H-INDOLE

(R)-5-bromo-3-[(1-methyl-2-pyrrolidinyl)methyl]-1H-indole

(R)-2-[(5-Bromo-1H-indol-3-yl)carbonyl]-1-pyrrolidinecarboxylic acid benzyl ester

(2R)-2-[(5-BroMo-1H-indol-3-yl)carbonyl]-1-pyrrolidinecarboxylic Acid PhenylMethyl Ester

InterMediate of Eletriptan

(R)-Benzyl 2-(5-bromo-1H-indole-3-carbonyl)-pyrrolidine-1-carboxylate

1-Pyrrolidinecarboxylic acid, 2-[(5-bromo-1H-indol-3-yl)carbonyl]-, phenylmethyl ester, (R)-

1-Pyrrolidinecarboxylic acid, 2-[(5-bromo-1H-indol-3-yl)carbonyl]-, phenylmethyl ester, (2R)-

(R)-(5-bromo-1H-indol-3-yl)[N-[(phenylmethoxy)carbonyl]-2-pyrrolidinyl]methanone

3-(N- benzyloxycarbonyl-D-prolyl)-5-bromoindole

(5R)3-(N-benzyloxycarbonyl-D-prolyl)-5-bromoindole

143322-56-9

163322-57-0

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