(R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole

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Products Intro: Product Name:(R)-5-Bromo-3-(N-methylpyrrolidine-2-ylmethyl)-1H-Indole
CAS:143322-57-0
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CAS:143322-57-0

(R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole manufacturers

(R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole Basic information
Product Name:(R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole
Synonyms:5-BROMO-3-(1-METHYL PYRROLIDIN-2-YL METHYL)-1H-INDOLE;1H-Indole,5-broMo-3-[[(2R)-1-Methyl-2-pyrrolidinyl]Methyl]-;(R)-5-BROMO-3-[(1-METHYL-2-PYRROLIDINYL)METHYL1]-1H-INDOLE;5-Bromo-3-(1-Methylpyrrolidin-2(R)-ylmethyl)-1H-Indole;5-bromo-3-[[(2R)-1-methyl-2-pyrrolidinyl]methyl]-1H-Indole;Eletriptan intermediate 2;(R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole;5-Bromo-3-[((2R)-1-methylpyrrolidin-2-yl)methyl]-1H-indole
CAS:143322-57-0
MF:C14H17BrN2
MW:293.2
EINECS:422-390-5
Product Categories:Chiral Reagents;Indole Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;API intermediates;Pharmaceutical material and intermeidates
Mol File:143322-57-0.mol
(R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole Structure
(R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole Chemical Properties
Boiling point 412.9±25.0 °C(Predicted)
density 1.418±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility DMSO (Slightly), Methanol (Slightly)
pka16.28±0.30(Predicted)
form Solid
color Off-White to Dark Yellow
Major Applicationpharmaceutical
InChIInChI=1S/C14H17BrN2/c1-17-6-2-3-12(17)7-10-9-16-14-5-4-11(15)8-13(10)14/h4-5,8-9,12,16H,2-3,6-7H2,1H3/t12-/m1/s1
InChIKeyJCXOJXALBTZEFE-GFCCVEGCSA-N
SMILESN1C2=C(C=C(Br)C=C2)C(C[C@H]2CCCN2C)=C1
CAS DataBase Reference143322-57-0(CAS DataBase Reference)
Safety Information
Hazard Codes T,N
Risk Statements 20/22-39-41-43-48/25-62-50/53
Safety Statements 53-45-60-61
WGK Germany WGK 3
HS Code 2933998350
Storage Class11 - Combustible Solids
MSDS Information
(R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole Usage And Synthesis
Chemical PropertiesLight Brown Solid
Uses5-Bromo Eletriptan is an impurity of Eletriptan (E505000), which is A serotonin 5-HTIB/ID receptor agonist, used for the treatment of migraine headaches.
Synthesis
1H-Indole, 5-bromo-3-[[(2R)-1-methyl-2-pyrrolidinyl]methyl]-, ethanedioate (1:1)

1196663-29-2

(R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole

143322-57-0

The general procedure for the synthesis of (R)-5-bromo-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indole from the compound (CAS:1196663-29-2) is as follows: Example 26; Preparation of BIP from BIP oxalate salt BIP oxalate (170 g, 0.4435 mol) and deionized water (1500 mL) were stirred at 15 °C. The pH was adjusted to 7.8 using aqueous sodium carbonate (70.5 g, 0.6650 mol, dissolved in 200 mL of deionized water.) Toluene (1000 mL) was added and stirred for 30 min at 30-35°C. The organic and aqueous layers were separated and the aqueous layer was extracted with toluene (500 mL). Separate the organic and aqueous layers again. The organic layer was combined and washed with 10% (w/v) sodium carbonate aqueous solution. After separating the organic and aqueous layers, the organic layer was concentrated to 70% of the original volume (~1050 mL) at 50-55°C under reduced pressure. The concentrate was gradually cooled to 5-10 °C with stirring to precipitate a solid product. The solid was collected by filtration and washed sequentially with cold toluene (100 mL) and n-heptane (100 mL). After drying, 117.0 g of product was obtained; yield: 90.5%; purity: 99.12% (as BIP).

References[1] Patent: US2009/299077, 2009, A1. Location in patent: Page/Page column 9-10
[2] Patent: WO2010/121673, 2010, A1. Location in patent: Page/Page column 21-23
[3] Patent: WO2012/25772, 2012, A1. Location in patent: Page/Page column 5
(R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole Preparation Products And Raw materials
Raw materials1H-Indole, 5-bromo-3-[[(2R)-1-methyl-2-pyrrolidinyl]methyl]-, ethanedioate (1:1)-->(R)-5-BROMO-3-[(1-METHYL-2-PYRROLIDINYL)METHYL]-1H-INDOLE-->Sodium carbonate-->Toluene
Preparation ProductsEletriptan hydrobromide
Tag:(R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole(143322-57-0) Related Product Information
Indometacin N-Methyl-2-pyrrolidone Kresoxim-methyl METSULFURON METHYL Methyl salicylate Thiophanate-methyl 5-[2-(benzenesulfonyl)ethyl]-3-[[(2R)-1-methyl-1-oxidopyrrolidin-1-ium-2-yl]methyl]-1H-indole Eletriptan Indole Indole-3-acetic acid Polyvinylpyrrolidone Tribenuron methyl 1-Hexadecylpyridinium bromide Methyl Methyl bromide Bromine (R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole bromo-Dragonfly

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