(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)

pka

16.28±0.30(Predicted)

form 

Solid

color 

Off-White to Dark Yellow

InChI

InChI=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

InChIKey

JCXOJXALBTZEFE-GFCCVEGCSA-N

SMILES

N1C2=C(C=C(Br)C=C2)C(C[C@H]2CCCN2C)=C1

CAS DataBase Reference

143322-57-0(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

HS Code 

2933998350

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

Chemical Properties

Light Brown Solid

Uses

5-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

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(143322-57-0)Related Product Information

• Indometacin
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• Indole-3-acetic acid
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• Bromine
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• bromo-Dragonfly