| Identification | More | [Name]
(R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole | [CAS]
143322-57-0 | [Synonyms]
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
Eletriptan intermediate | [EINECS(EC#)]
422-390-5 | [Molecular Formula]
C14H17BrN2 | [MDL Number]
MFCD00912970 | [Molecular Weight]
293.2 | [MOL File]
143322-57-0.mol |
| Chemical Properties | Back Directory | [Boiling point ]
412.9±25.0 °C(Predicted) | [density ]
1.418±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
16.28±0.30(Predicted) | [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 Data | Back Directory | [Hazard Codes ]
T,N | [Risk Statements ]
R20/22:Harmful by inhalation and if swallowed .
R39:Danger of very serious irreversible effects.
R41:Risk of serious damage to eyes.
R43:May cause sensitization by skin contact.
R48/25:Toxic: danger of serious damage to health by prolonged exposure if swallowed .
R62:Possible risk of impaired fertility.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [HS Code ]
2933998350 |
| Hazard Information | Back Directory | [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 |
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