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CAS No. : | 136117-69-6 | MDL No. : | MFCD06200984 |
Formula : | C9H8N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 176.17 g/mol | Pubchem ID : | - |
Synonyms : |
|
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: |
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* 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 |
---|---|---|
With hydrogenchloride; sodium hydrogencarbonate 1) H2O, a) r.t., 2.5 h, b) 80 deg C, 40 min, 2) r.t., overnight; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With sodium hydrogencarbonate at 60℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 74 percent / aq. LiOH / tetrahydrofuran / 0.5 h / 20 °C 2: EDCI / tetrahydrofuran / 20 °C 3: Burgess reagent / tetrahydrofuran / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 74 percent / aq. LiOH / tetrahydrofuran / 0.5 h / 20 °C 2: EDCI / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 17.2 percent / diisobutylaluminium hydride / CH2Cl2 / -60 °C 2: 11.9 percent / 1) n-butylamine, 1) ethylamine / ethanol / 32 h / Heating 3: 51.2 percent / Fe powder, FeCl2*(H2O)x, conc. HCl / ethanol; H2O / 1 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 17.2 percent / diisobutylaluminium hydride / CH2Cl2 / -60 °C 2: 11.9 percent / 1) n-butylamine, 1) ethylamine / ethanol / 32 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 17.2 percent / diisobutylaluminium hydride / CH2Cl2 / -60 °C 2: 11.9 percent / 1) n-butylamine, 1) ethylamine / ethanol / 32 h / Heating 3: 51.2 percent / Fe powder, FeCl2*(H2O)x, conc. HCl / ethanol; H2O / 1 h / Heating 4: 74.5 percent / dimethylformamide / 1 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 17.2 percent / diisobutylaluminium hydride / CH2Cl2 / -60 °C 2: 11.9 percent / 1) n-butylamine, 1) ethylamine / ethanol / 32 h / Heating 3: 51.2 percent / Fe powder, FeCl2*(H2O)x, conc. HCl / ethanol; H2O / 1 h / Heating 4: 74.5 percent / dimethylformamide / 1 h / 80 °C 5: 50.9 percent / NaOCH3 / dimethylformamide / 12 h / 80 - 90 °C 6: 50 percent / 85percent H3PO4 / 18 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 17.2 percent / diisobutylaluminium hydride / CH2Cl2 / -60 °C 2: 11.9 percent / 1) n-butylamine, 1) ethylamine / ethanol / 32 h / Heating 3: 51.2 percent / Fe powder, FeCl2*(H2O)x, conc. HCl / ethanol; H2O / 1 h / Heating 4: 74.5 percent / dimethylformamide / 1 h / 80 °C 5: 50.9 percent / NaOCH3 / dimethylformamide / 12 h / 80 - 90 °C 6: 55 percent / bromine / acetic acid / 0.5 h / 30 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With caesium carbonate; In N,N-dimethyl-formamide; | B. Imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester Cesium carbonate (15.7 g, 48.2 mmol) and iodomethane (1.50 ml, 24.2 mmol) were added to a solution of <strong>[139022-25-6]imidazo[1,2-a]pyridine-6-carboxylic acid</strong> (2.61 g, 16.1 mmol) in DMF (100 ml). The reaction was stirred at ambient temperature overnight, then poured into brine (100 ml) and extracted with ethyl acetate (3*100 mL). The combined organics were washed with saturated sodium bicarbonate solution (25 mL), and a 1N HCl solution (25 mL) then dried over MgSO4 and evaporated to give <strong>[139022-25-6]imidazo[1,2-a]pyridine-6-carboxylic acid</strong> methyl ester as a yellow solid (1.1 g, 39%). 1H NMR (250 MHz, CDCl3): delta 8.96 (s, 1H), 7.8-7.6 (m, 4H), 3.98 (s, 3H). MS [EI+] 177 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In ethyl acetate; acetonitrile; | C. 3-Iodo-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester N-iodosuccinamide (1.55 g, 6.89 mmol) was added to a solution of imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester (1.1 g, 6.24 mmol) in acetonitrile (50 mL) which had been cooled to 0 C. under a nitrogen atmosphere. The reaction stirred for 1 hr, then concentrated in vaccuo to a residue. The residue was dissolved in ethyl acetate (50 mL) and washed with 10% sodium bisulfate (2*10 ml) and brine (1*20 mL), then the organic layers were dried over MgSO4 and evaporated to give 3-iodo-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester as a pale yellow solid (1.79 g, 95%). 1H NMR (250 MHz, CDCl3): δ 8.91 (s, 1H), 7.85 (dd, 1H, J=2.5, J=10), 7.80 (s, 1H), 7.69 (d, 1H, J=10), 4.01 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | Stage #1: methyl 6-imidazo<1,2-a>pyridinecarboxylate With sodium hydride In toluene; mineral oil at 80℃; Stage #2: acetonitrile In toluene at 80℃; Stage #3: With hydrogenchloride In water; toluene | General procedure for aryl/heteroaryl β-ketonitrile synthesis (Al):[0149] Aryl or heteroaryl methyl carboxylate were commercially available or were synthesized according to the following standard procedure: the aryl or heteroaryl carboxylic acid (32 mmol) was dissolved in MeOH (40 mL) and sulfuric acid (1 mL) was added. The mixture was refluxed overnight, after which the solvent was evaporated under reduced pressure; the crude was dissolved in DCM and washed with saturated aqueous NaHCO3 solution. The organic phase was dried and evaporated under reduced pressure, and the crude was used without further purification.[0150] To a solution of an aryl or heteroaryl methyl carboxylate (6.5 mmol) in dry toluene (6 mL) under N2, NaH (50-60% dispersion in mineral oil, 624 mg, 13 mmol) was carefully added. The mixture was heated at 80 °C and then dry CH3CN was added dropwise (1.6 mL, 30.8 mmol). The reaction was heated for 18 hours and generally the product precipitated from the reaction mixture as Na salt.[0151] The reaction was then allowed to cool down to room temperature and the solid formed was filtered and then dissolved in water. The solution was then acidified with 2 N HCl solution and at pH between 2-6 (depending on the ring substitution on the aryl/heteroaryl system) the product precipitated and was filtered off. If no precipitation occurred, the product was extracted with DCM. [0152] After work-up, the products were generally used in the following step without further purification. The general yield was between 40 and 80%.; 3-Imidazo[l, 2-aJpyridin- 6-yl-3-oxo-propionitrile[0159] The product was obtained starting from imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester according to general procedure Al :Yield 39%C10H7N3O Mass (calculated) [185]; (found) [M+H+]=186 [M-H]=I 84LC Rt=O.23, 100% (3 min method)1H-NMR: (dmso-d6): 4.72 (2H,s), 7.61-7.65 (2H, m), 7.70 (1H, m), 8.07 (1H, s), 9.40 (s, 1H). |
Stage #1: methyl 6-imidazo<1,2-a>pyridinecarboxylate; acetonitrile With sodium hydride In toluene at 80℃; for 18h; Stage #2: With hydrogenchloride; water In toluene at 20℃; | To a solution of an aryl or heteroaryl methyl carboxylate (6.5 mmol) in dry toluene (6 mL) under N2, NaH (50-60% dispersion in mineral oil, 624 mg, 13 mmol) was carefully added. The mixture was heated at 800C and then dry CH3CN was added dropwise(1.6 mL, 30.8 mmol). The reaction was heated for 18 hours and generally the product precipitated from the reaction mixture as Na salt.The reaction was then allowed to cool down to room temperature and the solid formed was filtered and then dissolved in water. The solution was then acidified with 2N HCl solution and at pH between 2-6 (depending on the ring substitution on the aryl/heteroaryl system) the product precipitated and was filtered off. If no precipitation occurred, the product was extracted with DCM.After work-up, the products were generally used in the following step without further purification. The general yield was between 40 and 80%. | |
Stage #1: methyl 6-imidazo<1,2-a>pyridinecarboxylate With sodium hydride In toluene; mineral oil at 80℃; Heating / reflux; Stage #2: acetonitrile In toluene; mineral oil at 80℃; for 18h; Stage #3: With hydrogenchloride In water | Aryl or heteroaryl methyl carboxylate were commercially available or were synthesized according to the following standard procedure: the aryl or heteroaryl carboxylic acid (32 mmol) was dissolved in MeOH (40 mL) and sulfuric acid (ImL) was added. The mixture was refluxed overnight, after which the solvent was evaporated under reduced pressure; the crude was dissolved in DCM and washed with saturated aqueous NaHCO3 solution. The organic phase was dried and evaporated under reduced pressure, and the crude was used without further purification.To a solution of an aryl or heteroaryl methyl carboxylate (6.5 mmol) in dry toluene (6 mL) under N2, NaH (50-60% dispersion in mineral oil, 624 mg, 13 mmol) was carefully added. The mixture was heated at 80 0C and then dry CH3CN was added dropwise(1.6 mL, 30.8 mmol). The reaction was heated for 18 hours and generally the product precipitated from the reaction mixture as Na salt.[00164] The reaction was then allowed to cool down to room temperature and the solid formed was filtered and then dissolved in water. The solution was then acidified with 2N HCl solution and at pH between 2-6 (depending on the ring substitution on the aryl/heteroaryl system) the product precipitated and was filtered off. If no precipitation occurred, the product was extracted with DCM.[00165] After work-up, the products were generally used in the following step without further purification. The general yield was between 40 and 80%.; The product was obtained starting from imidazo[l,2-a]pyridine-6- carboxylic acid methyl ester according to general procedure AlYield 39%Ci0H7N3O Mass (calculated) [185]; (found) [M+H+]=186 [M-H]=I 84LC Rt=0.23, 100% (3 min method)IH-NMR: (dmso-d6): 4.72 (2H,s), 7.61-7.65 (2H, m), 7.70 (IH, m), 8.07 (IH, s), 9.40 (s,IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
sulfuric acid;Heating / reflux; | General procedure for aryl/heteroaryl beta-ketonitrile synthesis (Al):Aryl or heteroaryl methyl carboxylate were commercially available or were synthesized according to the following standard procedure: the aryl or heteroaryl carboxylic acid (32 mmol) was dissolved in MeOH (40 niL) and sulfuric acid (ImL) was added. The mixture was refluxed overnight, after which the solvent was <n="42"/>evaporated under reduced pressure; the crude was dissolved in DCM and washed with saturated aqueous NaHCO3 solution. The organic phase was dried and evaporated under reduced pressure, and the crude was used without further purification. | |
Aryl or heteroaryl methyl carboxylate were commercially available or were synthesized according to the following standard procedure: the aryl or heteroaryl carboxylic acid (32 mmol) was dissolved in MeOH (40 mL) and sulfuric acid (ImL) was added. The mixture was refluxed overnight, after which the solvent was evaporated under reduced pressure; the crude was dissolved in DCM and washed with saturated aqueous NaHCO3 solution. The organic phase was dried and evaporated under reduced pressure, and the crude was used without further purification.To a solution of an aryl or heteroaryl methyl carboxylate (6.5 mmol) in dry toluene (6 mL) under N2, NaH (50-60% dispersion in mineral oil, 624 mg, 13 mmol) was carefully <n="41"/>added. The mixture was heated at 80 0C and then dry CH3CN was added dropwise(1.6 mL, 30.8 mmol). The reaction was heated for 18 hours and generally the product precipitated from the reaction mixture as Na salt.[00164] The reaction was then allowed to cool down to room temperature and the solid formed was filtered and then dissolved in water. The solution was then acidified with 2N HCl solution and at pH between 2-6 (depending on the ring substitution on the aryl/heteroaryl system) the product precipitated and was filtered off. If no precipitation occurred, the product was extracted with DCM.[00165] After work-up, the products were generally used in the following step without further purification. The general yield was between 40 and 80%.; The product was obtained starting from imidazo[l,2-a]pyridine-6- carboxylic acid methyl ester according to general procedure AlYield 39%Ci0H7N3O Mass (calculated) [185]; (found) [M+H+]=186 [M-H]=I 84LC Rt=0.23, 100% (3 min method)IH-NMR: (dmso-d6): 4.72 (2H,s), 7.61-7.65 (2H, m), 7.70 (IH, m), 8.07 (IH, s), 9.40 (s,IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With hydrazine hydrate Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With sodium hydrogencarbonate In methanol for 8h; Reflux; | |
63% | In ethanol; water for 4h; Reflux; | |
In ethanol for 18h; Heating / reflux; | N1 To a solution of 50% aq. chloroacetaldehyde (1.1 eq, 36 mmol, 4.6 ml) in ethanol (120 ml) is added 6-amino-nicotinic acid methyl ester (1 eq, 33 mmol, 5 g) at room temperature. The reaction mixture is heated at reflux for 18 hours. The solvent is removed in vacuo and the crude product is dissolved in water (400 ml). The aqueous solution is treated with sodium bicarbonate to pH = 8 and extracted with DCM (3 x 250 ml). The organic layer is dried (MgSO4) and evaporated to give the title compound as a beige solid. |
Stage #1: 2-chloroethanal; methyl 6-aminonicotinoate In ethanol; water for 4h; Reflux; Stage #2: With sodium hydrogencarbonate In water | To a solution of Z-1 (9.0 g, 59.21 mmol) in anhydrous EtOH (160 ml) was added chloroacetaldehyde (40% in H2O, 48.6 mL, 296 mmol). The reaction mixture was refluxed for 4h, then concentrated. The residue was dissolved in water and adjusted to pH>7 with a saturated NaHC03 solution, extracted with EtOAc and purified by silica gel chromatography to afford the title compound (6.60 g). MS (m/z): 177 (M+1 )+. | |
In ethanol; water for 4h; Reflux; | Methyl H-imidazo[1,2-a]pyridine-6-carboxylate (Z-2) To a solution of Z-1 (9.0 g, 59.21 mmol) in anhydrous EtOH (160 ml) was added chloroacetaldehyde (40% in H2O, 48.6 mL, 296 mmol). The reaction mixture was refluxed for 4 h, then concentrated. The residue was dissolved in water and adjusted to pH>7 with a saturated NaHCO3 solution, extracted with EtOAc and purified by silica gel chromatography to afford the title compound (6.60 g). MS (m/z): 177 (M+1)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bromine; In acetic acid; at 20℃; for 1.0h; | To Imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester (1 eq, 33 mmol, 5.8 g) in acetic acid (60 ml) under an inert atmosphere of argon is added dropwise bromine (1 eq, 33 mmol, 1.7 ml). After stirring at room temperature for 1 hour, the reaction mixture is filtered to afford the title compound as a beige solid; [M+H]+ =255/257 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | Step 1: Methyl H-imidazo [1, 2-a] pyridine-6-carboxylate (288) [0443] A solution of 2- (BROMOMETHYL)-1, 3-DIOXOLANE (0.18 mL; 1.67 MMOL) in THF (3 mL) and water (0.2 mL) was treated with concentrated HCI (3 drops) and stirred at 88C for 50 min. The solution was cooled down to 0C and transferred into a vial containing 2-amino-5- METHOXYCARBONYLPYRIDINE (287,204mg ; 1. 34MMOL), BU2SNCI2 (134 mg; 0.40 MMOL) and NAHC03 (410 mg) and stirred at room temperature for 2 days. The reaction mixture was diluted with ethyl acetate (60mL) and washed with saturated aqueous sodium chloride. The organic layer was dried (MGS04), filtered and concentrated. After chromatographic purification of the residue using preparative TLC on silica gel (eluent 50% ethyl acetate in dichloromethane), the title compound 288 was obtained (74 mg, 31% YIELD). H NMR: (500.7 MHz, CDCI3) 6 (PPM) : 9. 00 (S, 1H); 7.80 (m, 4H); 4.00 (s, 3H). MS: CALC : 176.1 ; found: 177.1 (M+H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 5%-palladium/activated carbon; acetic acid at 50℃; for 16h; | 342.A methyl 5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6-carboxylate (1069) To a 50 ml pressure bottle were placed methyl imidazo[1,2-a]pyridine-6-carboxylate (0.26 g), acetic acid (10 ml), and wet 5% palladium on carbon (0.052 g). The reaction mixture was stirred for 16 hours at 30 psi and 50° C. The solid was filtered off, and the filtrate was concentrated. The residue was taken up in ethyl acetate. It was then washed with saturated sodium bicarbonate, brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel using 10-100% ethyl acetate in hexanes to provide the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With isopropylmagnesium chloride In tetrahydrofuran at -20℃; for 1h; Inert atmosphere; | |
Stage #1: methyl 6-imidazo<1,2-a>pyridinecarboxylate; N,0-dimethylhydroxylamine With isopropylmagnesium bromide In tetrahydrofuran at -20℃; for 1h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; water | To a mixture of Z-2 (5.0 g, 28.4 mmol) and N-methoxymethanamine (5.54 g, 56.8 mmol) in dry THF (50 ml) at -20°C under N2 was added isopropylmagnesium chloride (56.8 mL, 1 13.6 mmol) over 30 mins. The resulting mixture was stirred at -20°C for 30 mins, then quenched with 20% N H4CI solution, and extracted with EtOAc (50 mL *3). The combined organic layers were dried over Na2S04, concentrated and purified by silicon gel chromatography to afford the title compound (3.0 g). MS (m/z): 206 (M+1 )+. | |
With isopropylmagnesium chloride In tetrahydrofuran at -20℃; for 1h; Inert atmosphere; | N-Methoxy-N-methylH-imidazo[1,2-a]pyridine-6-carboxamide (Z-3) To a mixture of Z-2 (5.0 g, 28.4 mmol) and N-methoxymethanamine (5.54 g, 56.8 mmol) in dry THF (50 ml) at -20° C. under N2 was added isopropylmagnesium chloride (56.8 mL, 113.6 mmol) over 30 mins. The resulting mixture was stirred at -20° C. for 30 mins, then quenched with 20% NH4Cl solution, and extracted with EtOAc (50 mL*3). The combined organic layers were dried over Na2SO4, concentrated and purified by silicon gel chromatography to afford the title compound (3.0 g). MS (m/z): 206 (M+1)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C 2: manganese(IV) oxide / dichloromethane / 5 h / Reflux 3: acetic acid; 3-amino propanoic acid / 2 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | Stage #1: methyl 6-imidazo<1,2-a>pyridinecarboxylate With lithium hydroxide monohydrate; water In methanol at 20 - 60℃; Stage #2: With ammonium chloride; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In methanol at 20℃; for 2h; | 19.19a (19a) Imidazo[1,2-a]pyridine-6-carboxamide (19a) Imidazo[1,2-a]pyridine-6-carboxamide Into methanol / water (3 / 1, 40 mL), methyl imidazo[1,2-a]pyridine-6-carboxylate (1.00 g, 5.68 mmol) was dissolved, to which lithium hydroxide monohydrate (286 mg, 6.82 mmol) was added, followed by stirring at room temperature for 45 minutes, and then at 60°C overnight. The resulting reaction liquid was left to cool, to which ammonium chloride (911 mg, 17.0 mmol) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (3.14 g, 11.4 mmol) were added, followed by stirring at room temperature for two hours. To the reaction liquid, water and dichloromethane were added for extraction, and the resulting aqueous layer was further extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. After filtration, the residue thus obtained was purified by basic silica gel column chromatography (hexane : ethyl acetate = 50 : 50, V/V, dichloromethane : methanol = 90 : 10, V/V) to give the desired title compound (0.37 g, yield 40%). 1H-NMR (DMSO-D6) δ: 7.51 (1H, br s), 7.59 (1H, d, J = 9.2 Hz), 7.64-7.67 (2H, m), 8.05-8.07 (2H, m), 9.12-9.13 (1H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / dichloromethane / 12 h / 20 °C 2: sodium hydroxide / tetrahydrofuran / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-Bromosuccinimide / dichloromethane / 12 h / 20 °C 2: sodium hydroxide / tetrahydrofuran / 2 h / 20 °C 3: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 20 °C 4: triethylamine / dichloromethane / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N-Bromosuccinimide / dichloromethane / 12 h / 20 °C 2: sodium hydroxide / tetrahydrofuran / 2 h / 20 °C 3: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 20 °C 4: triethylamine / dichloromethane / 0.5 h / 20 °C 5: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 12 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / dichloromethane / 12 h / 20 °C 2: sodium hydroxide / tetrahydrofuran / 2 h / 20 °C 3: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 2.1: tetrahydrofuran / 0 - 20 °C 3.1: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0 °C 4.1: ammonium hydroxide; triphenylphosphine / tetrahydrofuran / 20 °C 5.1: N-ethyl-N,N-diisopropylamine / 130 °C / Sealed tube 6.1: acetic acid; sodium nitrite / water / 1.5 h / 0 °C 6.2: 20 °C 7.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / water; 1,4-dioxane / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 2: tetrahydrofuran / 0 - 20 °C 3: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0 °C 4: ammonium hydroxide; triphenylphosphine / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 2: tetrahydrofuran / 0 - 20 °C 3: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0 °C 4: ammonium hydroxide; triphenylphosphine / tetrahydrofuran / 20 °C 5: N-ethyl-N,N-diisopropylamine / 130 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 2.1: tetrahydrofuran / 0 - 20 °C 3.1: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0 °C 4.1: ammonium hydroxide; triphenylphosphine / tetrahydrofuran / 20 °C 5.1: N-ethyl-N,N-diisopropylamine / 130 °C / Sealed tube 6.1: acetic acid; sodium nitrite / water / 1.5 h / 0 °C 6.2: 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 2: tetrahydrofuran / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 2: tetrahydrofuran / 0 - 20 °C 3: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 2: tetrahydrofuran / 0 - 20 °C 3: sodium tetrahydroborate / ethanol / 1 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 2.1: tetrahydrofuran / 0 - 20 °C 3.1: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0 °C 4.1: ammonium hydroxide; triphenylphosphine / tetrahydrofuran / 20 °C 5.1: N-ethyl-N,N-diisopropylamine / 130 °C / Sealed tube 6.1: acetic acid; sodium nitrite / water / 1.5 h / 0 °C 6.2: 20 °C 7.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / water; 1,4-dioxane / 110 °C / Inert atmosphere 8.1: Chiralpak / ethanol; 2,2'-iminobis[ethanol] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In N,N-dimethyl-formamide at 80℃; for 1h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrahydrofuran; diethyl ether / 2 h / 0 - 20 °C / Inert atmosphere 2: triphenylphosphine; palladium diacetate; potassium carbonate / ethanol; 1,4-dioxane / 18 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: tetrahydrofuran; diethyl ether / 2 h / 0 - 20 °C / Inert atmosphere 2: triphenylphosphine; palladium diacetate; potassium carbonate / ethanol; 1,4-dioxane / 18 h / 100 °C / Inert atmosphere 3: methanesulfonato (2-dicyclohexylphosphino-2’,6’- di-isopropoxy-1,1‘-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl)palladium(II); Cs2CO3 / tetrahydrofuran / 2 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: tetrahydrofuran; diethyl ether / 2 h / 0 - 20 °C / Inert atmosphere 2: triphenylphosphine; palladium diacetate; potassium carbonate / ethanol; 1,4-dioxane / 18 h / 100 °C / Inert atmosphere 3: methanesulfonato (2-dicyclohexylphosphino-2’,6’- di-isopropoxy-1,1‘-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl)palladium(II); Cs2CO3 / tetrahydrofuran / 2 h / 80 °C / Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; diethyl ether at 0 - 20℃; for 2h; Inert atmosphere; | 3.A Step A.2-(imidazo[1,2-a]pyridin-6-yl)propan-2-ol To a cooled 0oC solution of methyl imidazo[1,2-a]pyridine-6-carboxylate (1.0 g, 5.7 mmol) in tetrahydrofuran (20 mL) was added a solution of methyl magnesium bromide in diethyl ether (3.0 M, 7.57 mL, 22.7 mmol). The resulting reaction mixture was allowed to warm to 20 °C and stirred for 2 hours. The reaction was then cooled to 0oC, quenched by addition of water (20 mL), and extracted with ethyl acetate (2 x 15). The combined organic extracts were washed with saturated aqueous sodium chloride solution (2 x 15 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide the title compound: LCMS m/z 177.2 [M+H]+. |
Tags: 136117-69-6 synthesis path| 136117-69-6 SDS| 136117-69-6 COA| 136117-69-6 purity| 136117-69-6 application| 136117-69-6 NMR| 136117-69-6 COA| 136117-69-6 structure
[ 957120-91-1 ]
Methyl imidazo[1,2-a]pyridine-6-carboxylate hydrochloride
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[ 957120-91-1 ]
Methyl imidazo[1,2-a]pyridine-6-carboxylate hydrochloride
Similarity: 0.98
[ 133427-07-3 ]
Methyl imidazo[1,2-a]pyridine-8-carboxylate
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[ 158001-04-8 ]
Ethyl imidazo[1,2-a]pyridine-6-carboxylate
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[ 158020-74-7 ]
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[ 86718-01-6 ]
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