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7-Chloro-3-iodo-1,5-dihydroimidazo[1,2-a]pyridine
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[ CAS No. 908267-60-7 ] {[proInfo.proName]}

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Chemical Structure| 908267-60-7
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CAS No. :908267-60-7 MDL No. :MFCD12400825
Formula : C7H6ClIN2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 280.49 Pubchem ID :-
Synonyms :

Safety of [ 908267-60-7 ]

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Application In Synthesis of [ 908267-60-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 908267-60-7 ]

[ 908267-60-7 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 4532-25-6 ]
  • [ 908267-60-7 ]
YieldReaction ConditionsOperation in experiment
73% With N-iodo-succinimide; In acetonitrile; for 0.5h; Preparation 22; 3-Iodo-7-chloro-imidazo[l,2,a]pyridineTo a solution of 7-chloro-imidazo[l,2,a]pyridine (6.10 g, 40 mmol) (Yamanaka, Motosuke et al., Chemical & Pharmaceutical Bulletin (1991), 39(6), 1556-67) in dry acetonitrile (100 mL), add N-iodosuccinamide. Stir for 30 minutes. Filter off the precipitate and then wash with acetonitrile. Recrystallize the precipitate from acetonitrile to give a white solid. Concentrate the filtrate, dilute with ethyl acetate, wash with 10% sodium hydrogensulfite (NaHSO3), saturated aqueous sodium bicarbonate, saturated aqueous NaCl, dry over MgSO4, filter and evaporate. Use the combined solid without further purification (8.0 g, 73%). 1H NMR (DMSO) delta 8.33 (d, IH, J = 7.3 Hz), 7.79 (d, IH, J = 2.0 Hz), 7.72 (s, IH), 7.07 (dd, IH, J = 7.3 and 2.0 Hz).
50% With N-iodo-succinimide; In N,N-dimethyl-formamide; at 20℃; for 6h; Synthesis of 7-Chloro-3-iodoimidazo [1 ,2-a]pyridine (compound 65-4)[0000230] To a solution of compound 65-3 (450 mg, 2.9 mmol, 1 equiv) in dimethyl formamide (4.5 mL) was added Niodosuccinimide (700 mg, 3.1 mmol, 1.05 equiv) . The reaction was stirred at room temperature for 6 hours followed by the addition of water (20 ml) and ethyl acetate (20 ml) . The layers were separated and the aqueous phase was extracted with ethyl acetate (3 x 5 ml) . The organic layers were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to a black residue. The residue from 2 runs was chromatographed on an AnaLogix 8g column using a gradient of 0-70% ethyl acetate in heptanes. The product containing fractions were combined and washed with saturated sodium thiosulfate solution (2 x 20 ml) to remove the remaining iodine color. The fractions were concentrated to give compound 65-4 as a white solid (829 mg, 50% yield)
38% With N-iodo-succinimide; In acetonitrile; at 20℃; for 3h; (2b) 7-Chloro-3-iodoimidazo[1,2-a]pyridine Into acetonitrile (40 mL), <strong>[4532-25-6]7-chloroimidazo[1,2-a]pyridine</strong> (635 mg, 4.16 mmol) produced in Example 2 (2a) was dissolved, to which N-iodosuccinimide (936 mg, 4.16 mmol) was added, followed by stirring at room temperature for three hours. A solid precipitated, which was collected by filtration and purified by basic silica gel column chromatography (dichloromethane : ethyl acetate = 4 : 1, V/V) to give the desired title compound (436 mg, yield 38%). 1H-NMR (CDCl3) 5: 6.92 (1H, dd, J = 7.3, 1.8 Hz), 7.63 (1H, d, J = 1.8 Hz), 7.69 (1H, s), 8.06 (1H, d, J = 7.3 Hz).
With N-iodo-succinimide; In N,N-dimethyl-formamide; at 20℃; Procedure A2 - General iodination; To a solution of 7-Chloro-imidazo[1 ,2-a]pyridine (30.9 g, 186 mmol, 1.0 equiv) in DMF (280ml) was added N-iodosuccinimide (43.6 g, 194 mmol, 1.05 equiv) and the resulting mixture was stirred overnight at RT. The thin brown slurry was diluted with water (840ml), brine (280ml) and extracted with EtOAc (560 ml). The aqueous layer was further extracted with EtOAc (3 x 280ml). The combined organic phases were washed with water (2 x 280ml), 10%w/v sodium thiosulfate (280 ml), brine (280 ml), dried (MgSO4), filtered and concentrated in vacuo to give a brown residue. The residue was triturated with ether (200ml), filtered and the solid was washed with ether (2 x 50ml) and dried on the filter to give 39 g of product.
With N-iodo-succinimide; In N,N-dimethyl-formamide; at 20℃; To a solution of 7-Chloro-imidazo[1 ,2-a]pyridine (30.9 g, 186 mmol, 1.0 equiv) in DMF (280ml) was added N-iodosuccinimide (43.6 g, 194 mmol, 1.05 equiv) and the resulting mixture was stirred overnight at RT. The thin brown slurry was diluted with water (840ml), brine (280ml) and extracted with EtOAc (560 ml). The aqueous was further extracted with EtOAc (3 x 280ml). The combined organic phases were washed with water (2 x 280ml), 10%w/v sodium thiosulfate (280 ml), brine (280 ml), dried (MgSO4) and concentrated in vacuo to give a brown residue. The residue was triturated with ether (200ml), filtered and the solid was washed ether (2 x 50ml) and dried on the filter to give 39 g of product. MS: [M+H]+ 279
1.58 g With N-iodo-succinimide; In N,N-dimethyl-formamide; at 20℃; for 16h; To a solution of 7-chloroimidazo[l,2-a]pyridine (7.78 mmol, 1.0 eq) in DMF (12 mL) at rt was added N-iodosuccinimide (1.84 g, 8.17 mmol, 1.05 eq). After 16 h, the brown slurry was diluted with H2O (100 mL) and Brine (15 mL). The mixture was extracted with EtOAc (100 mL). The aqueous layer was re-extracted with EtOAc (100 mL) and the collected organic layers were washed with H2O (2 x 20 mL), 10% sodium thiosulfate (20 mL), Brine (20 mL) and dried (MgSC ). After filtration, the solution was concentrated. The residue was triturated with diethyl ether (15 mL) and filtered to afford an off-white solid (1.58 g, 73% yield over 2 steps). (0246) LCMS: RT = 0.265 min, >98% 215 and 254 nM, m/z = 279.0 [M + H]+.
With N-iodo-succinimide; In N,N-dimethyl-formamide; at 20℃; To a solution of 7-Chloro-imidazo[1 ,2-a]pyridine (30.9 g, 186 mmol, 1.0 equiv) in DMF (280ml) was added N-iodosuccinimide (43.6 g, 194 mmol, 1.05 equiv) and the resulting mixture was stirred overnight at RT. The thin brown slurry was diluted with water (840ml), brine (280ml) and extracted with EtOAc (560 ml). The aqueous layer was further extracted with EtOAc (3 x 280ml). The combined organic phases were washed with water (2 x 280ml), 10%w/v sodium thiosulfate (280 ml), brine (280 ml), dried (MgSO4), filtered and concentrated in vacuo to give a brown residue. The residue was triturated with ether (200ml), filtered and the solid was washed with ether (2 x 50ml) and dried on the filter to give 39 g of product. MS: [M+H]+ = 279.

Reference： [1]Patent: WO2006/91671,2006,A1 .Location in patent: Page/Page column 25
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 750 - 756
[3]Patent: WO2013/123215,2013,A2 .Location in patent: Paragraph 0000230
[4]Patent: EP2565185,2013,A1 .Location in patent: Paragraph 0116
[5]Patent: WO2008/78100,2008,A2 .Location in patent: Page/Page column 93-94
[6]Patent: WO2009/47506,2009,A1 .Location in patent: Page/Page column 111
[7]Patent: WO2018/136634,2018,A1 .Location in patent: Page/Page column 41
[8]Patent: WO2009/150240,2009,A1 .Location in patent: Page/Page column 101
  • 2
  • [ 908267-60-7 ]
  • [ 22237-13-4 ]
  • [ 1421589-68-5 ]
YieldReaction ConditionsOperation in experiment
70% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 90℃; for 3h;Inert atmosphere; Synthesis of 7-Chloro-3- (4-ethoxyphenyl) imidazo[1 , 2-a]pyridine (compound 65-5)[0000231] A suspension of compound 65-4 (200 mg, 0.72 mmol, 1 equiv), Pd(PPh3)4 (41 mg, 0.036 mmol, 0.05 equiv), 4- ethoxyphenylboronic acid (121.5 mg, 0.73 mmol, 1.02 equiv), and sodium carbonate (152 mg, 1.4 mmol, 2 equiv) in 3:1 mixture of dioxane and water (20 mL) was degassed with a stream of nitrogen for 10 minutes. The reaction was heated at 90 C for 3 h, at which time LC-MS indicated the reaction was complete. Ethyl acetate (10 mL) was added and the layers were separated. The organic layer was dried over sodium sulfate, filtered through silica gel (2g) and the silica gel was washed with ethyl acetate (15 mL) . The filtrates were evaporated under reduce pressure and the product was triturated with methyl tert-butyl ether (3 mL) to give compound 65-5 as an off white solid. (130 mg, 70% yield)
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 750 - 756
[2]Patent: WO2013/123215,2013,A2 .Location in patent: Paragraph 0000231
  • 3
  • [ 282116-97-6 ]
  • [ 908267-60-7 ]
  • [ 1345687-68-4 ]
YieldReaction ConditionsOperation in experiment
50% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In dichloromethane at 100℃; for 2.5h; Inert atmosphere; 2.2c (2c) Ethyl [4-(7-chloroimidazo[1,2-a]pyridin-3-yl)phenoxy]acetate (2c) Ethyl [4-(7-chloroimidazo[1,2-a]pyridin-3-yl)phenoxy]acetate N,N-Dimethylformamide (5 mL) was added to 7-chloro-3-iodoimidazo[1,2-a]pyridine (436 mg, 1.57 mmol) synthesized in Example 2 (2b), [4-(2-ethoxy-2-oxoethoxy)phenyl]boronic acid (386 mg, 1.72 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (128 mg, 0.157 mmol), and potassium carbonate (649 mg, 4.70 mmol), followed by stirring at 100°C for 2.5 hours under an argon atmosphere. The resulting mixture was left to cool, to which ethyl acetate and water were added. Insoluble matters were filtered off and the resulting solution was subjected to extraction. The resulting organic layer was dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the residue thus obtained was purified by basic silica gel column chromatography (hexane : ethyl acetate = 2 : 1, V/V) to give the desired title compound (260 mg, yield 50%). 1H-NMR (CDCl3) δ: 1.33 (3H, t, J = 7.3 Hz), 4.30 (2H, q, J = 7.3 Hz), 4.70 (2H, s), 6.78 (1H, dd, J = 7.3, 1.8 Hz), 7.06 (2H, d, J = 8.0 Hz), 7.45 (2H, d, J = 8.0 Hz), 7.61 (1H, s), 7.64-7.65 (1H, m), 8.16 (1H, d, J = 7.3 Hz).
Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - EP2565185, 2013, A1 Location in patent: Paragraph 0117
  • 4
  • [ 516-12-1 ]
  • [ 4532-25-6 ]
  • [ 908267-60-7 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2793 - 2800

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