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[ CAS No. 1187236-18-5 ] {[proInfo.proName]}

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Chemical Structure| 1187236-18-5
Chemical Structure| 1187236-18-5
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Product Details of [ 1187236-18-5 ]

CAS No. :1187236-18-5 MDL No. :MFCD11505036
Formula : C10H9BrN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZNBQFCWFNJYWEE-UHFFFAOYSA-N
M.W : 269.09 Pubchem ID :51063904
Synonyms :

Safety of [ 1187236-18-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1187236-18-5 ]

* 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 [ 1187236-18-5 ]

[ 1187236-18-5 ] Synthesis Path-Downstream   1~22

  • 1
  • [ 84249-14-9 ]
  • [ 70-23-5 ]
  • [ 1187236-18-5 ]
YieldReaction ConditionsOperation in experiment
90% In ethanol; for 8h;Reflux; To a solution of <strong>[84249-14-9]4-bromopyridin-2-amine</strong> (5.00 g, 28.9 mmol) in EtOH (50 mL) was added ethyl 3-bromo-2-oxopropanoate (12.02 g, 61.6 mmol). The reaction mixture was stirred at reflux for 8 h and concentrated in vacuo. The residue was purified by a silica gel column chromatography (MeOH/DCM (v/v) = 1/10) to give the title compound as a pale yellow solid (7.02 g, 90percent).MS (ESI, pos, ion): 269.1 [M+H]+;
40% With p-toluenesulfonic acid monohydrate; In ethanol; at 100℃; To <strong>[84249-14-9]4-bromopyridin-2-amine</strong> (6.00 g, 34.7 mmol)Add in EtOH (100mL) suspensionP-toluenesulfonic acid monohydrate (1.32g, 6.94mmol)And ethyl 3-bromo-2-oxopropanoate (10.14 g, 52.00 mmol).The mixture is placed in a sealed tube,It was then heated to 100 ° C and stirred overnight.After the reaction,The reaction mixture was concentrated under reduced pressure.The residue obtained was diluted with aq. sat. Na2CO3 (50 mL) and water (30mL).The resulting mixture was extracted with DCM (100 mL×3).The combined organic phases were dried over anhydrous sodium sulfate.Filter and concentrate under reduced pressure.The residue obtained is purified by silica gel column chromatography (EtOAc/EtOAc (v/v) = 1/10 to 1/5 to 1/2).The title compound was obtained as a pale yellow solid (3.80 g, yield 40percent).
In acetonitrile; at 20 - 150℃; for 1.5h; 0.6 g (3.47 mmol) of <strong>[84249-14-9]2-amino-4-bromopyridine</strong>, 1.55 g (7.15 mmol) of ethyl bromopyruvate and 4 mL of acetonitrile are placed in a 20 mL screw-topped tube equipped with a magnetic bar. The top is then screwed on and the tube is stirred at room temperature for 1 hour, and then heated at 150 C. with stirring for 30 minutes. After this time and cooling to room temperature, the precipitate obtained is filtered off, rinsed with acetonitrile and dried. The filtrate is concentrated to dryness and then purified by chromatography on a column of silica gel, eluting with a mixture of dichloromethane and methanol. The solid obtained after evaporating off the solvent is dried under reduced pressure. 530 mg of the expected product are obtained in total.1H NMR (DMSO-D6), delta ppm: 8.65 (s, 1H); 8.6 (d, 1H); 8.05 (s, 1H); 7.3 (m, 1H); 4.3 (q, 2H); 1.3 (t, 3H).
6.5 g In toluene; at 115℃; for 16h; Step 1 Preparation of 7-Bromo-imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester To a stirred solution of 4-Bromo-pyridin-2-ylamine (4 g, 23.12 mmol) in toluene (40 mL) is added 3-Bromo-2-oxo-propionic acid ethyl ester (4.5 g, 23.12 mmol). The reaction mixture is heated at 115 C. for 16 hours. Reaction mixture is cooled to 0 C. then diluted with water and extract with ethyl acetate. Organic layer is dried over sodium sulphate, solvent is evaporated in vacuo to afford the title compound (6.5 g). 1H-NMR (400 MHz, DMSO-d6) delta: 1.31 (t, J=7.2 Hz, 3H), 4.26-4.33 (q, J=7.2 Hz, 2H), 7.18-7.20 (dd, J1=1.92 Hz, J2=7.16 Hz, 1H), 7.98 (s, 1H), 8.53 (d, J=7.32 Hz, 1H), 8.57 (s, 1H). LC-MS (m/z): [M+H]=271.0.
To a solution of 258-1 (2.477 g, 14.3 mmol) in THF (40 ml) is added AU-1 (2.20 ml, 15.8 mmol), and the mixture is heated at reflux for 2 h. A solution of TEA (5 ml) in ethanol (15 ml) is added. After stirring for 2 h at 80 C, the mixture is cooled to ambient temperature, and filtered. The residue is dissolved in EtOAc, washed with water, and concentrated. The residue is purified on SiO2 (0-70% EtOAC in heptane) to give 258-2.

  • 2
  • [ 1187236-18-5 ]
  • [ 1187236-21-0 ]
YieldReaction ConditionsOperation in experiment
To a suspension of 0.25 g (0.93 mmol) of <strong>[1187236-18-5]ethyl 7-bromoimidazo[1,2-a]pyridine-2-carboxylate</strong>, prepared according to the protocol described in step 8.1, in 4 mL of anhydrous dichloromethane, stirred at -19 C. under an inert atmosphere, are added dropwise 2.09 mL (2.09 mmol) of a molar solution of DIBAL-H in toluene. The reaction mixture is stirred at -19 C. for 3 hours and then hydrolysed at -40 C. by successive addition of 0.1 mL of methanol, 0.1 mL of water and 10 mL of 5N HCl. The reaction mixture is then basified with aqueous sodium hydroxide solution (24%) and then extracted with three times 100 mL of dichloromethane. The combined organic phases are dried over sodium sulfate and then concentrated under reduced pressure. The crude reaction product is then purified by chromatography on a column of silica gel, eluting with a mixture of dichloromethane and methanol. 110 mg of the expected product are thus obtained.1H NMR (DMSO-D6), delta ppm: 8.0 (d, 1H); 7.8 (s, 1H); 7.6 (s, 1H); 6.9 (m, 1H); 4.9 (s, 2H).
0.340 g With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 1h; Step 2 Preparation of 7-Bromo-imidazo[1,2-a]pyridin-2-yl)-methanol To a stirred solution of 7-Bromo-imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester (3.3 g, 12.26 mmol) in tetrahydrofuran (30 mL) is added lithium aluminium hydride (2M solution in tetrahydrofuran) (5.8 mL, 12.26 mmol). Reaction mixture is stirred 0 C. for 1 hour. The reaction mixture is diluted with ethyl acetate and the mixture is filtered through Buckner funnel. The residue is dissolved in saturated solution of sodium bicarbonate and extracted with 10% methanol in CH2Cl2 (30 mL). Organic layer is dried over sodium sulfate, and solvent is evaporated in vacuo to give crude material, purified by column chromatography eluting in 3% MeOH:CH2Cl2 to afford the title compound (0.340 g). 1H-NMR (400 MHz, DMSO-d6) delta: 4.57 (d, J=5.76 Hz, 2H), 5.22 (t, J=5.68 Hz, 1H), 7.00-7.02 (dd, J1=1.96 Hz, J2=7.12 Hz, 1H), 7.76 (d, J=1.64 Hz, 1H), 7.82 (s, 1H), 8.48 (d, J=7.2 Hz, 1H). LC-MS (m/z): [M+H]=227.0.
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 25℃; for 16h;Schlenk technique; To a solution of ethyl 7-bromoimidazo[l,2-a]pyridine-2-carboxylate (400 mg, 1.486 mmol) in dry THF (3 mL) at 0 0 C was added L1AIH4 (56.4 mg, 1.486 mmol) in a schlenk tube. After the mixture stirred for 16 hours at 25C, TLC indicated the reaction was completed. The mixture was diluted with saturated aqueous H4CI (20 mL) and extracted with ethyl acetate (70 mL x 3). The combined organic layers were washed with water (40 mL) and brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography (pet. ether/ethyl acetate) to give the title compound.
  • 3
  • [ 1187236-18-5 ]
  • [ 1019023-07-4 ]
  • 4
  • [ 1187236-18-5 ]
  • [ 886371-82-0 ]
  • 5
  • [ 1187236-18-5 ]
  • [ 1454907-25-5 ]
  • 6
  • [ 1187236-18-5 ]
  • [ 1454907-26-6 ]
  • 7
  • [ 1187236-18-5 ]
  • [ 1454907-27-7 ]
  • 8
  • [ 1187236-18-5 ]
  • [ 1454904-55-2 ]
  • 9
  • [ 1187236-18-5 ]
  • [ 1419211-50-9 ]
  • [ 1541189-93-8 ]
YieldReaction ConditionsOperation in experiment
With 2-Picolinic acid; potassium phosphate; copper(l) iodide; In dimethyl sulfoxide; at 90℃;Inert atmosphere; A mixture of 258-2 (300 mg, 1.12 mmol), B (356 mg, 1.23 mmol), Cul (21 mg, 0.11 mmol), K3PO4 (473 mg, 2.23 mmol), and picolinic acid (28 mg, 0.22 mmol) in DMSO (6 ml) is sparged with N2 for 5 min, and heated at 90 C overnight. The reaction mixture is cooled to ambient temperature, diluted with EtOAc and water, and filtered. The filtrate is washed with water and brine. The organic layer is dried, concentrated, and purified Si02 (0-6%, MeOH in DCM) to give 258-3
  • 10
  • [ 1187236-18-5 ]
  • [ 1541187-87-4 ]
  • 11
  • [ 1187236-18-5 ]
  • [ 1541189-94-9 ]
  • 12
  • [ 1187236-18-5 ]
  • [ 1541189-95-0 ]
  • 13
  • [ 1187236-18-5 ]
  • 7-bromo-2-(fluoromethyl)imidazo[1,2-a]pyridine [ No CAS ]
  • 14
  • [ 1187236-18-5 ]
  • 2-(fluoromethyl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine [ No CAS ]
  • 15
  • [ 1187236-18-5 ]
  • 5-(1-((1-fluorocyclopentyl)methyl)-1H-pyrazol-4-yl)-6-(2-(fluoromethyl)imidazo[1,2-a]pyridin-7-yl)picolinonitrile [ No CAS ]
  • 16
  • [ 1187236-18-5 ]
  • 7-bromoimidazo[1,2-a]pyridine-2-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With diisobutylaluminium hydride; In dichloromethane; at -78℃;Inert atmosphere; To a suspension of ethyl 7-bromoimidazo[l,2-a]pyridine-2-carboxylate (3.50 g, 13.0 mmol) in anhydrous DCM (80 mL) was added diisobutyl aluminum hydride (18.50 mL, 18.50 mmol, 1.0 M) at -78 C under N2 atmosphere. The mixture was stirred at -78 C overnight and then moved to 0 C, and quenched with water (0.75 mL), 15% NaOH aqueous solution (0.75 mL) and another water (2 mL) successively. The resulting mixture was stirred at rt for 15 min. To the mixture were added Et20 (50 mL), EtOAc (50 mL) and hydrous Mg2S04 (20 g), stirred for 15 min, filtered. The filter cake was washed with EtOAc (200 mL), the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v) = 1/10 to 1/5) to afford the title compound as a light-yellow solid (1.50 g, 51%).MS (ESI, pos. ion) m/z: 225.0 [M+H]+;1H NMR (400 MHz, CDCl3) d (ppm): 10.14 (s, 1H), 8.13 (s, 1H), 8.04 (d, J= 7.2 Hz, 1H), 7.89 (s, 1H), 7.02 (dd, j= 7.2, 1.7 Hz, 1H).
51% With diisobutylaluminium hydride; In dichloromethane; at -78 - 0℃;Inert atmosphere; Under the protection of -78 C and N2,To <strong>[1187236-18-5]ethyl 7-bromoimidazo[1,2-a]pyridine-2-carboxylate</strong> (3.50 g, 13.0 mmol)Add in anhydrous DCM (80 mL) suspensionDiisobutylaluminum hydride (18.50 mL, 18.50 mmol, 1.0 M).The mixture was stirred at -78 C overnight.After the reaction is over, move to 0 C.And add water (0.75mL) in turn.15% NaOH aqueous solution (0.75mL)The reaction was quenched with water (2 mL).The resulting mixture was stirred at room temperature for 15 minutes.Then add Et2O (50 mL),EtOAc (50 mL) and Mg 2 SO 4 (20 g).Continue stirring for 15 minutes and filter again.The resulting filter cake was rinsed with EtOAc (200 mL).The filtrate was concentrated under reduced pressure.The residue obtained was purified by silica gel column chromatography (EtOAc /EtOAcTo give the title compound as a pale yellow solid (1.50g, 51% yield).
  • 17
  • [ 1187236-18-5 ]
  • 7-bromo-2-(difluoromethyl)imidazo[1,2-a]pyridine [ No CAS ]
  • 18
  • [ 1187236-18-5 ]
  • 2-(difluoromethyl)-N-(diphenylmethylene)imidazo[1,2-a]pyridin-7-amine [ No CAS ]
  • 19
  • [ 1187236-18-5 ]
  • 2-(difluoromethyl)imidazo[1,2-a]pyridin-7-amine [ No CAS ]
  • 20
  • [ 1187236-18-5 ]
  • 6-(4-((5-chloro-2-((2-(difluoromethyl)imidazo[1,2-a]pyridin-7-yl)amino)pyrimidin-4-yl)amino)piperidin-1-yl)pyridazine-3-carbonitrile [ No CAS ]
  • 21
  • [ 1187236-18-5 ]
  • 7-aminoimidazo[1,2-a]pyridin-2-carboxylic acid ethyl ester [ No CAS ]
  • 22
  • [ 1013-88-3 ]
  • [ 1187236-18-5 ]
  • 7-((diphenylmethylene)amino)imidazo[1,2-a]pyridin-2-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; for 6h;Reflux; Inert atmosphere; To a solution of ethyl 7-bromoimidazo[l,2-a]pyridine-2-carboxylate (8.0 g, 30.0 mmol) and diphenylmethanimine (8.10 g, 45.0 mmol) in l,4-dioxane (100 mL) were added Pd2(dba)3 (2.76 g, 3.0 mmol), BINAP (1.84 g, 3.0 mmol) and CS2CO3 (19.60 g, 60.3 mmol). The reaction mixture was stirred at reflux for 6 h under N2 atmosphere, cooled down to rt and filtered. The filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtO Ac/PE (v/v) = 1/2) to give the title compound as a pale yellow solid (5.20 g, 47%). MS (ESI, pos, ion): 370.2 [M+H]+.
47% With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; for 6h;Inert atmosphere; Reflux; toEthyl 7-bromoimidazo[1,2-a]pyridine-2-carboxylate(8.0g, 30.0mmol)And benzophenone imine (8.10g, 45.0mmol) in 1,4-dioxane (100mL) solutionPd2(dba)3 (2.76g, 3.0mmol), BINAP (1.84g, 3.0mmol) andCs2CO3 (19.60 g, 60.3 mmol).The reaction system was refluxed under a nitrogen atmosphere and stirred for 6 hours, then cooled to room temperature and filtered.The resulting filtrate was concentrated under reduced pressure. Residue obtainedPurified by silica gel column chromatography (EtOAc /EtOAc(5.20 g, 47%).
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