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[ CAS No. 878197-68-3 ]

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Chemical Structure| 878197-68-3
Chemical Structure| 878197-68-3
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Product Details of [ 878197-68-3 ]

CAS No. :878197-68-3 MDL No. :MFCD11226918
Formula : C8H5BrN2O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :225.04 g/mol Pubchem ID :57355077
Synonyms :

Safety of [ 878197-68-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 878197-68-3 ]

  • Upstream synthesis route of [ 878197-68-3 ]
  • Downstream synthetic route of [ 878197-68-3 ]

[ 878197-68-3 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 921-03-9 ]
  • [ 878197-68-3 ]
YieldReaction ConditionsOperation in experiment
72% With hydrogenchloride In 1,2-dimethoxyethane; water at 10 - 75℃; To a solution of X4-019-4 (3.0 g, 1.73 mol) and DME (120 ml) was added X4-019-4a (5.6 g, 3.03 mol) in one portion at room temperature, the reaction mixture was stirred at65 °C for 4 hours. After being cooled down to 10 °C, the mixture was stirred for 1 hour and filtered. After washing with DME, The filtered solid was suspended in DME (120 ml) and 2 M HC1 aq. (120 ml), and stirred overnight at 75 °C. After being cooled down to 10 °C, the mixture was neutralized with 3 M NaOH aq. to pH = 8 and filtered. The filtered cake was washed with water and dried in vacuum at 50 °C to give X4-019-5 as an off-white solid (2.81 g, 72percent yield). LC-MS (Agilent LCMS 1200-6110, Mobile Phase: from 95percent [water + 0.05percent TFA] and 5percent [CH3CN + 0.05percent TFA] to 0percent [water + 0.05percent TFA] and 100percent [CH3CN + 0.05 percent TFA] in 1.6 mm, then under this condition for 1.4 mm, finally changed to 95percent [water + 0.05percent TFA] and 5percent [CH3CN + 0.05percent TFA] in 0.05 mm and under this condition for 0.7 mi. Purity: 94.5percent, Rt = 1.26 mm; MS Calcd.: 223.96; MS Found: 225.1 [M+H]t
Reference: [1] Patent: WO2017/223239, 2017, A1, . Location in patent: Paragraph 00377; 00378
  • 2
  • [ 19798-81-3 ]
  • [ 921-03-9 ]
  • [ 878197-68-3 ]
YieldReaction ConditionsOperation in experiment
72% at 25 - 65℃; for 2 - 4 h; The reactor is charged with 2-amino-6-bromopyridine (3.0 Kg, 17.3 mol) and dimethoxyethane ( 12 Liters) and stirred under nitrogen. 1,1,3-Trichloroacetone (5.6 Kg, 30.3 mol) is added to the 25° C solution in a single portion and the reaction solution is warmed to 65 0C jacket temperature and maintained for approximately 2 to 4 hours until judged complete. The reaction is cooled to 10° C and held for approximately one hour and filtered. The solids are rinsed with dimethoxyethane (6 Liters). The solid is placed back in the reactor and treated with dimethoxyethane (12 Liters) and 2N HCI (12 Liters) and warmed to aproximately 75 degrees for 16 to 20 hours or until judged complete. The reaction is cooled to approximately 1O0C and pH is adjusted to approximately 8 with 3 N NaOH. The resulting solids are filtered and washed with water. The solid is dried at 500C for 16 hours to yield 5- bromoimidazo[1 ,2-a]pyridine-2-carbaldehyde, (2.81 Kg, 72percent yield) 1H NMR (400 MHz, DMSO-D6) δ ppm 10.05 (s, 1 H) 8.66 (s, 1 H) 7.72 (s, 1 H) 7.42 (s, 1 H) 7.35 (S, 1 H)
50%
Stage #1: at 70℃; for 15 h;
Stage #2: for 7 h; Heating / reflux
Stage #3: With calcium carbonate In water for 1.5 h; Heating / reflux
To a solution of 2-amino-6-bromopyridine (10 g, 58 mmol) in ethylene glycol dimethyl ether (66 mL) was added trichloroacetone (18 mL, 173 mmol). The mixture was stirred at 7O0C for 15 hours and the resulting precipitate was collected by filtration and refluxed in ethyl alcohol (50 mL) for 7 hours. The reaction mixture was cooled to room temperature, concentrated, dissolved in dichloromethane, and washed with saturated aqueous sodium bicarbonate. The organic layer was isolated, dried with magnesium sulfate, and concentrated. The resulting solid was refluxed in aqueous calcium carbonate for 1.5 hours, cooled to room temperature, and extracted with dichloromethane. The organic layer was dried with magnesium sulfate and concentrated to give 6.6 g (50percent yield) 5-bromoimidazo[1 ,2-a]pyridine-2- carbaldehyde as an orange solid. 1H-NMR (CDCI3): δ 10.16 (s, 1H), 8.37 (s, 1 H), 7.69 (d, 1H)1 7.22 (m, 1H), 7.16 (m, 1 H); TLC (10percent ammonium hydroxide- acetonitrile) Rf = 0.44.
Reference: [1] Organic Process Research and Development, 2009, vol. 13, # 4, p. 781 - 785
[2] Patent: WO2007/87549, 2007, A2, . Location in patent: Page/Page column 49
[3] Patent: WO2007/87549, 2007, A2, . Location in patent: Page/Page column 39-40
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