Identification | Back Directory | [Name]
(2R)-2-(2,5-DIFLUOROPHENYL)PYRROLIDINE | [CAS]
1218935-59-1 | [Synonyms]
Larotrectinib Pyrrolidine Impurity (R)-2-(2,5-difluorophenyl)pyrrolidine (2R)-2-(2,5-DIFLUOROPHENYL)PYRROLIDINE (2R)-2-(2,5-DIFLUOROPHENYL)PYRROLIDINE-HCL Pyrrolidine, 2-(2,5-difluorophenyl)-, (2R)- (2R)-2-(2,5-Difluorophenyl)pyrrolidine hydrochloride Larotrectinib Impurity 7(Larotrectinib Pyrrolidine Impurity) | [EINECS(EC#)]
227-251-0 | [Molecular Formula]
C10H11F2N | [MDL Number]
MFCD07772701 | [MOL File]
1218935-59-1.mol | [Molecular Weight]
183.2 |
Chemical Properties | Back Directory | [Boiling point ]
213.5±40.0 °C(Predicted) | [density ]
1.164±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [pka]
9.02±0.10(Predicted) | [Appearance]
Light yellow to yellow Liquid |
Hazard Information | Back Directory | [Uses]
(2R)-2-(2,5-Difluorophenyl)pyrrolidine is used in the synthesis of imidazo[1,2-b]pyridazine compounds as inhibitors of Trk kinases. | [Synthesis]
GENERAL STEPS: To a solution of (R)-1-((S)-tert-butylsulfinyl)-2-(2,5-difluorophenyl)pyrrolidine (8.60 g, 29.9 mmol) in methanol (60 mL) was slowly added a dioxane solution (37.4 mL, 150 mmol) of 4M hydrochloric acid at 0 °C. The reaction mixture was stirred at room temperature for 12 hours. After completion of the reaction, the mixture was concentrated under vacuum and the residue was dissolved in water (100 mL) and washed with ethyl acetate (100 mL). The aqueous layer was separated and neutralized with 1N aqueous sodium hydroxide (150 mL) followed by extraction with dichloromethane (100 mL × 3). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuum to afford (R)-2-(2,5-difluorophenyl)pyrrolidine (5.06 g, 92% yield) as a slightly reddish oil.1H-NMR (CDCl3, Varian, 400 MHz): δ 1.56-1.65 (1H, m), 1.78-1.93 (3H m), 2.21-2.30 (1H, m), 3.01-3.08 (1H, m), 3.13-3.18 (1H, m), 4.39 (1H, t, J = 7.6 Hz), 6.82-6.88 (1H, m), 6.91-6.97 (1H, m), 7.22-7.26 (1H, m). | [References]
[1] Patent: CN107286070, 2017, A. Location in patent: Paragraph 0079; 0080; 0081 [2] Patent: US2016/168156, 2016, A1. Location in patent: Paragraph 0207; 0215; 0216 [3] Patent: CN109053525, 2018, A. Location in patent: Paragraph 0021; 0031; 0032; 0033 [4] Patent: CN108003161, 2018, A. Location in patent: Paragraph 0324; 0325; 0345-0347 |
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