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CAS No. : | 6188-23-4 | MDL No. : | MFCD06496200 |
Formula : | C7H5BrN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FXPMFQUOGYGTAM-UHFFFAOYSA-N |
M.W : | 197.03 | Pubchem ID : | 2795547 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 42.89 |
TPSA : | 17.3 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.76 cm/s |
Log Po/w (iLOGP) : | 1.97 |
Log Po/w (XLOGP3) : | 2.45 |
Log Po/w (WLOGP) : | 2.1 |
Log Po/w (MLOGP) : | 1.48 |
Log Po/w (SILICOS-IT) : | 1.67 |
Consensus Log Po/w : | 1.93 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.27 |
Solubility : | 0.106 mg/ml ; 0.000536 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.46 |
Solubility : | 0.688 mg/ml ; 0.00349 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.94 |
Solubility : | 0.225 mg/ml ; 0.00114 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.62 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: for 3 h; Reflux Stage #2: With sodium hydrogencarbonate In water |
(1) Preparation of 6-bromoimidazo[1,2-a]pyridine (4) 2.00 g of 2-amino-5-bromopyridine (3) is dissolved in ethanol (35 mL), and chloroacetaldehyde in water (2.52 mL, 6.1 mol/L) was added and the reaction mixture was heated at reflux for 3 hours. The reaction mixture was concentrated, and saturated aqueous NaHCO3 was added to the residue, and it is extracted with ethyl acetate. After conventional workup afford 2.30 g of the titled compound as a brown powder (yield: 100percent). LCMS (ESI) m/z (M+H)+: 368.93 |
100% | at 80℃; for 15 h; | To a solution of 5-bromopyridin-2-amine (10.0 g, 57.7 mmol) in EtOH/H2O (100 mL/20 mL) was added 2-chloroacetaldehyde (10.5 g, 86.7 mmol) slowly. The mixture was heated to 80° C. and stirred further for 15 hours, then cooled to rt and concentrated in vacuo. The saturated aqueous NaHCO3 solution (200 mL) was added to the residue. The resulted mixture was extracted with DCM (200 mL*3). The combined organic phases were concentrated in vacuo to give the title compound as a brown solid (11.3 g, 100percent). MS (ESI, pos. ion) m/z: 197.1 [M+H]+. |
98% | for 6 h; Reflux | The scheme above describes the synthesis of a compound of the invention. A substituted pyridine such as compound 1-1 is reacted with 2-chloroacetaldehyde, resulting in the halogenated imidazopyridine compound 1-2. |
98% | for 6 h; Reflux | j0554] The scheme above describes the synthesis of a compound of the invention. A substituted pyridine such as compound 1-1 is reacted with 2-chloroacetaldehyde, resulting in the halogenated imidazopyridine compound 1-2. Compound 1-2 is coupled to a benzoxazolyl boronic acid ester in Suzuki conditions to produce compound 1-4. Further derivatization of compound 1-4 using, for example, NBS, DMF results in halogenation of the imidazopyridine moiety, which is then further reacted in an additional Suzuki coupling using pyridine boronic acid to result in compound 1-6. |
83% | With sodium hydrogencarbonate In water; isopropyl alcohol at 80℃; for 72 h; | 2-Amino-5-bromopyridine (Aldrich, 18.8 g, 108.7 mmol), chloroacetaldehyde (34 mL of 50percent solution in water, 217.4 mmol), NaHCO3 (20.1 g, 239.1 mmol) and i-PrOH (150 mL) were combined in a sealed tube, purged with N2, sealed and heated to 80 0C. After 72 h, the mixture was cooled to rt and concentrated under reduced pressure. The residue was diluted with EtOAc, washed with water and brine and the combined aqueous layers were back-extracted with EtOAc. The combined extracts were dried over Na2SO4 and decolorizing carbon, filtered through a pad of Celite.(R). and concentrated under reduced pressure. The residue was purified by silica gel chromatography (75 to 85percent EtOAc/hexanes to give 17.85 g (83percent) of the title compound as a tan solid. MS(ES)+ m/e 198.7 [M+H]+. |
83% | for 14 h; Heating / reflux | Reflux a solution OF 2-AMINO-5-BROMO-PYRIDINE (Maybridge; 1.0 g, 5.78 mmol), 50percent aqueous chloroacetaldehyde (2 mL, 12.7 mmol) in acetonitrile (100 mL) for 14 h. Dilute the reaction with saturated aqueous sodium bicarbonate and extract into ethyl acetate. Flash chromatography using appropriate ethyl acetate/hexane mixtures gives 0.95 g (83percent) of the subtitled compound as a tan solid. MS (electrospray, m/z) 196.7, 198.7 (M+1). 1H NMR (400 MHz, DMSO-d6) 8 8.9 (d, J= 1. 5 Hz, 1H), 7.90 (s, 1H), 7.58 (d, J = 1.5 Hz, 1H), 7.53 (d, J = 9. 2 HZ, 1H), 7.29 (dd, J = 9. 2, 2 HZ, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64.28% | Stage #1: With hydrogenchloride; sodium acetate In ethanol; water for 2.5 h; Reflux Stage #2: With sodium hydrogencarbonate In water |
To a stirred solution of 5-bromo-pyridin-2-amine (5 g, 28.9 mmol) and sodium acetate (4.0 g, 48.76 mmol) in 100 mL of 60 percent ethanol in water, was added a refluxed solution of sodium acetate (2.0 g, 24.38 mmol) followed by 2-chloro-1 ,1 -dimethoxyethane (6.66 g, 53.5 mmol) in concentrated hydrochloric acid (1 .0 mL) in water (6 mL) and the reaction mass was refluxed for 2.5 h. The solvent was removed, residue obtained was diluted with cold water and pH adjusted to neutral (~7) with saturated sodium bicarbonate solution. The reaction mixture was extracted with ethyl acetate (2x100 mL), washed with water (2x100 mL) and brine (2x100 mL) and dried over anhydrous sodium sulphate. The crude material obtained was purified by trituration using 2 percent ethyl acetate in petroleum ether. Yield: 3.6 g (64.28 percent); 1H NMR (DMSO-d6, 300 MHz): δ 7.33 (dd, 1 H, J=1 .8, 9.6 Hz, Ar), 7.55 (d, 1 H, J=9.6 Hz, Ar), 7.60 (s, 1 H, Ar), 7.92 (s, 1 H, Ar), 8.91 (s, 1 H, Ar); MS (ES+): m/e 198 (M+1 ). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With sulfuric acid; nitric acid In water at 20℃; for 0.25 h; | To a solution of 6-bromoimidazo[1,2-a]pyridine (100 mg, 0.508 mmol) in concentrated H2SO4 (0.4 ml) was added at rt concentrated HNO3 (0.12 ml, 2.69 mmol) and the reaction mixture was stirred for 15 min. The mixture was quenched by the addition of ice and the resulting solid (123 mg, 99percent) was collected by filtration and used directly in the next step without further purification. 1H NMR (500 MHz, DMSO) δ 9.40 (t, J=1.4 Hz, 1H), 8.78 (s, 1H), 8.00-7.85 (m, 2H); MS (ESI) [M+H]+ 242.1/244.1; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With N-iodo-succinimide In acetonitrile at 20℃; for 1 h; | To a solution of 6-bromoimidazo[1,2-a]pyridine (721 mg 3.66 mmol) in 20 mL ACN were added 988 mg (4.39 mmol) of N-iodosuccinimide. The reaction was stirred at room temperature for 1 h. Solvent was removed in vacuo then residue was diluted with CH2Cl2 and washed successively with 10percent NaOH aqueous solution, saturated thiosulfate solution and then with water. The organic layer was dried over magnesium sulfate and concentrated in vacuo to afford the desired product as a white solid (1.18 g), 96percent yield, mp 209 °C; IR (ATR) ν (cm-1) 3024. 1516. 711. 698. 1H NMR (400 MHz, CDCl3) δ 7.29 (dd, J=9.6, 1.8 Hz, 1H), 7.51 (d, J=9.6 Hz, 1H), 7.70 (s, 1H), 8.26-8.28 (m, 1H). 13C NMR (100.6 MHz, CDCl3) δ 61.4, 108.4, 118.6, 126.4, 128.6, 128.6, 141.1, 146.5. HRMS (EI) m/z calcd for C7H4BrIN2 [M+H]+: 322.8675, found: 322.8678. |
77% | With N-iodo-succinimide In acetonitrile for 16.0833 h; | To a slightly cloudy mixture of 6-bromoimidazo[l,2-α]pyridine (15.4 g, 78.0 mmol) in dry MeCN (500 mL) was added jV-iodosuccinimide (17.6 g, 78.0 mmol) portionwise over ~5 min (a precipitate immediately formed). After 16 h, the crude product was collected by filtration and triturated with boiling MeCN to provide 19.56 g (77percent) of the title compound as an off-white solid. MS(ES)+ m/e 198.7 [M+H]+. |
67% | With N-iodo-succinimide In acetonitrile at 20℃; for 5 h; | Step: 1 To a solution of 6-bromoimidazo [l ,2-a]pyridine (20 g, 101.5 mmol) in ACN (300 mL) was added N-iodosuccinimide (22.8 g, 101.5 mmol) at rt and stirred for 5 h. The reaction mixture was filtered and washed with hot acetonitrile to afford 6-bromo-3-iodoimidazo[l,2- ajpyridine (22 g, 67percent) as a pale yellow solid. 1H NMR (400 MHz, CDC13) δ 8.29 (s, 1H), 7.58 (d, J= 9.2 Hz, 1H), 7.35 (d, J= 7.6 Hz, 1H), 7.27 (s, 1H). |
67% | With N-iodo-succinimide In acetonitrile at 20℃; for 5 h; | To a solution of 6-bromoimidazo[1,2-a]pyridine (20 g, 101.5 mmol) in ACN (300 mL) was added N-iodosuccinimide (22.8 g, 101.5 mmol) at rt and stirred for 5 h. The reaction mixture was filtered and washed with hot acetonitrile to afford 6-bromo-3-iodoimidazo[1,2-a]pyridine (22 g, 67percent) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.29 (s, 1H), 7.58 (d, J=9.2 Hz, 1H), 7.35 (d, J=7.6 Hz, 1H), 7.27 (s, 1H). |
51% | With N-iodo-succinimide In acetonitrile at 20℃; for 1 h; | To a solution of 6-bromoimidazo[1,2-a]pyridine (5 g, 25.4 mmol) in CH3CN (139 mL) was added NIS (6.85 g, 30.5 mmol). The reaction was stirred at r.t. for 1 hour and the reaction was concentrated. The residue was diluted with DCM (140 mL) and washed with 100 mL of 10 percent NaOH, 100 mL of saturated thiosulfate solution, and then 100 mL of water. The organic layer was dried over MgSO4, filtered and concentrated. The material was isolated as a beige solid (4.163 g, 51 percent yield).1H NMR (400 MHz, CDCl3) δ 8.28– 8.27 (m, 1H), 7.69 (s, 1H), 7.51 (dd, J = 1.2, 12.8 Hz, 1H), 7.29 (dd, J = 2.8, 12.8 Hz, 1H). This material had spectra that were indistinguishable from the literature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With tris-(dibenzylideneacetone)dipalladium(0); sodium acetate; tricyclohexylphosphine In 1,4-dioxane at 115 - 120℃; for 24 h; | 20.0 g of compound vii (0.102 mol), 38.7 g of bis(pinacolato)diboron (0.152 mol), 2.85 g of tricyclohexyl phosphine (0.010 mol), 4.65 g of tris(dibenzylideneacetone)dipalladium (0.005 mol) and 25.0 sodium acetate were added to 200ml 1,4-dioxane, heated to 115 ~ 120 , incubation reaction 24h, cooling to room temperature, adding purified water 200ml. Extracted twice with 200 ml of ethyl acetate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a reddish brown solid. The solid was added to 30 ml of t-butyl methyl ether, stirred for 2 h. A yellowish solid, i.e. 9-azoindole-5-boronic acid (compound vi), was filtered off and weighed 11.8 g in a yield of 72.0percent. |
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