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CAS No. : | 1093418-75-7 | MDL No. : | MFCD16877107 |
Formula : | C8H6BrIO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VAYKANWZAJRNOM-UHFFFAOYSA-N |
M.W : | 340.94 | Pubchem ID : | 58484707 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | 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 |
---|---|---|
90% | at 60℃; for 2 h; | Into a 250-mE round-bottom flask, was placed methyl 4-bromo-2-iodobenzoate (5.8 g, 17.01 mmol, 1.00 equiv), NMP (60 mE), CuCN (1.82 g, 20.45 mmol, 1.20 equiv). The resulting solution was stirred for 2 hours at 60° C. in an oil bath. The resulting solution was extracted with ethyl acetate (50 mEx2) and the organic layers combined. The resulting mixture was washed with Fe504 (aq.) (50 mEx2). The mixture was dried over anhydrous sodium sulfate. The residue was applied onto a silica gel colunm with ethyl acetate/petroleum ether (1/3). This resulted in 3.68 g (90percent) of methyl 4-bromo-2-cyanobenzoate as a white solid. |
2.39 g | at 60℃; for 1 h; | [0363] Preparation Example 75: Preparation of methyl 4-bromo-2-cyanobenzoate[0364][0365] To a mixture of methyl 4-bromo-2-iodobenzoate (3.52 g) described in Preparation Example 74 and coppercyanide (1.16 g) was added N-methylpyrrolidone (21 mL), and the mixture was stirred at 60°C for 1 hr. The reactionmixture was cooled, a solution of saturated aqueous ammonium chloride solution and aqueous ammonia (1:1) wasadded, and the mixture was extracted with ethyl acetate. The organic layer was washed with a solution of saturatedaqueous ammonium chloride solution and aqueous ammonia (1:1), saturated aqueous ammonium chloride solution,and saturated brine. The organic layer was dried over sodium sulfate, and the solvent was evaporated to give the titlecompound (2.39 g).MS (ESI) m/z:240(M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: 4-methoxycarbonylphenyl bromide With cadmium(II) chloride-N,N,N',N'-tetramethylethylenediamine; 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; hexane at 20℃; for 2h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane Inert atmosphere; regioselective reaction; | |
60% | Stage #1: 4-methoxycarbonylphenyl bromide With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; cadmium(II) chloride-N,N,N',N'-tetramethylethylenediamine In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane Inert atmosphere; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene for 24h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; | 34.1 Example 34; N-{4-[3-tert-Butyl-1-(6-methyl-2-oxo-1,2-dihydro-pyridin-3-yl)-isoquinolin-6-yl]-phenyl}-methanesulfonamide (I-48); step 1-; To a solution 150a (5.93 g, 17.4 mmol), Pd(PPh3)2Cl2 (610 mg, 870 mmol), CuI (0.331 g, 1.74 mmol) and THF (178 mL) was added TEA (14.1 g, 19.4 mL, 139 mmol). The reaction mixture was degassed with Ar and then 3,3-dimethylbut-1-yne was added to the mixture. The mixture was stirred at RT overnight then diluted with ether and washed with H2O. The organic extract was washed with 2N HCl and sat. AQ. NaHCO3, dried (Na2SO4), filtered and concentrated. The crude material was purified by SiO2 chromatography eluting with an EtOAc/hexane (0 to 10% EtOAc) to afford 150b. NMR indicated the product contained 10% of starting material. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | Methyl 2-amino-4-brombenzoate (10 g, 43.47 mmol) is suspended in sulphuric acid 20% (200 mL) and obtained solution is cooled down to 0 C. Sodium nitrite (3.60 g, 52.16 mmol), dissolved in water (40 mL), is added dropwise between 0 C.-5 C. and the reaction mixture is stirred for further 40 minutes at this temperature. Afterwards a cooled solution (ca. 0 C.) of potassium iodide (14.43 g, 86.93 mmol) in water (40 mL) is added dropwise and the reaction mixture is stirred for 1 h at 5 C. The reaction mixture is poured onto ice-water and extracted with ethyl acetate. The organic layer is washed with water, 10% aq. sodium thiosulfate solution, brine, dried over Na2SO4 and concentrated in vacuo. Yield 94%. | |
81% | Into a 1000-mE 3-necked round-bottom flask, was placed <strong>[135484-83-2]methyl 2-amino-4-bromobenzoate</strong> (5.0 g, 21.73 mmol, 1.00 equiv), a solution of sulfuric acid (20%) (20 mE) in water (100 mE). This was followed by the addition of a solution of NaNO2 (1.8 g, 26.09 mmol, 1.20 equiv) in water (20 mE) dropwise with stirring at 00 C., after stirred 1 hour at 00 C. To this was added a solution of iodopotassium (7.21 g, 43.43 mmol, 2.00 equiv) in water (30 mE) dropwise with stirring at 00 C. The resulting solution was stirred for 1 hour at 00 C. in a water/ice bath. The reaction was then quenched by the addition of 200 mE of water/ice. The resulting solution was extracted with ethyl acetate (100 mEx3) and the organic layers combined. The resulting mixture was washed with brine (100 mExl). The residue was applied onto a silica gel colunm with ethyl acetate/petroleum ether (1/5). This resulted in 5.97 g (81%) of methyl 4-bromo-2-iodobenzoate as light yellow oil. | |
7.05 g | [0360] Preparation Example 74: Preparation of methyl 4-bromo-2-iodobenzoate[0361][0362] To <strong>[135484-83-2]methyl 2-amino-4-bromobenzoate</strong> (5.75 g) was added cooled 20% sulfuric acid (75 mL), sodium nitrite (2.07g) was added by small portions under ice-cooling, and the mixture was stirred at the same temperature for 40 min. ToEP 2 565 182 A142510152025303540455055this reaction mixture was added dropwise a solution of potassium iodide (8.3 g) in water (25 mL) under cooling to 5C,20% sulfuric acid (30 mL) was added, and the mixture was stirred at 5C for 2 hr. This reaction mixture was neutralizedwith 4N aqueous sodium hydroxide solution under ice-cooling, 10% aqueous sodium sulfite solution (45 mL) and sodiumchloride were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with 10% aqueoussodium sulfite solution added saturated brine and saturated brine, dried over sodium sulfate, and the solvent wasevaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound(7.05 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In 1-methyl-pyrrolidin-2-one; at 60℃; for 2h; | Into a 250-mE round-bottom flask, was placed methyl 4-bromo-2-iodobenzoate (5.8 g, 17.01 mmol, 1.00 equiv), NMP (60 mE), CuCN (1.82 g, 20.45 mmol, 1.20 equiv). The resulting solution was stirred for 2 hours at 60 C. in an oil bath. The resulting solution was extracted with ethyl acetate (50 mEx2) and the organic layers combined. The resulting mixture was washed with Fe504 (aq.) (50 mEx2). The mixture was dried over anhydrous sodium sulfate. The residue was applied onto a silica gel colunm with ethyl acetate/petroleum ether (1/3). This resulted in 3.68 g (90%) of methyl 4-bromo-2-cyanobenzoate as a white solid. |
2.39 g | In 1-methyl-pyrrolidin-2-one; at 60℃; for 1h; | [0363] Preparation Example 75: Preparation of methyl 4-bromo-2-cyanobenzoate[0364][0365] To a mixture of methyl 4-bromo-2-iodobenzoate (3.52 g) described in Preparation Example 74 and coppercyanide (1.16 g) was added N-methylpyrrolidone (21 mL), and the mixture was stirred at 60C for 1 hr. The reactionmixture was cooled, a solution of saturated aqueous ammonium chloride solution and aqueous ammonia (1:1) wasadded, and the mixture was extracted with ethyl acetate. The organic layer was washed with a solution of saturatedaqueous ammonium chloride solution and aqueous ammonia (1:1), saturated aqueous ammonium chloride solution,and saturated brine. The organic layer was dried over sodium sulfate, and the solvent was evaporated to give the titlecompound (2.39 g).MS (ESI) m/z:240(M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | Stage #1: diethyl (bromodifluoromethyl)phosphonate With zinc In 1,4-dioxane at 60℃; for 3h; Inert atmosphere; Stage #2: With copper(l) iodide; 1,10-Phenanthroline In 1,4-dioxane at 20℃; for 0.5h; Inert atmosphere; Stage #3: methyl 4-bromo-2-iodobenzoate In 1,4-dioxane at 60℃; for 48h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: isopropylmagnesium chloride/lithium chloride complex / tetrahydrofuran / 1.08 h / -70 - 20 °C 2: lithium borohydride / tetrahydrofuran / 20 °C 3: hydrogenchloride / tetrahydrofuran; water / 30 h / 90 °C 4: acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 0.92 h / 20 °C 5: sodium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; acetone / 0.75 h / 80 °C / Inert atmosphere; Microwave irradiation | ||
Multi-step reaction with 5 steps 1: isopropylmagnesium chloride/lithium chloride complex / tetrahydrofuran / 1.08 h / -70 - 20 °C 2: lithium borohydride / tetrahydrofuran / 20 °C 3: hydrogenchloride / tetrahydrofuran; water / 30 h / 90 °C 4: acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 0.92 h / 20 °C 5: sodium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; acetone / 1.5 h / 80 °C / Inert atmosphere | ||
Multi-step reaction with 6 steps 1: isopropylmagnesium chloride/lithium chloride complex / tetrahydrofuran / 1.08 h / -70 - 20 °C 2: lithium borohydride / tetrahydrofuran / 20 °C 3: triethylamine; p-toluenesulfonylanhydride / tetrahydrofuran / 0 - 20 °C 4: trifluoroacetic acid / dichloromethane / 1.17 h / 20 °C 5: acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 0.92 h / 20 °C 6: sodium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; acetone / 0.75 h / 80 °C / Inert atmosphere; Microwave irradiation |
Multi-step reaction with 6 steps 1: isopropylmagnesium chloride/lithium chloride complex / tetrahydrofuran / 1.08 h / -70 - 20 °C 2: lithium borohydride / tetrahydrofuran / 20 °C 3: triethylamine; p-toluenesulfonylanhydride / tetrahydrofuran / 0 - 20 °C 4: trifluoroacetic acid / dichloromethane / 1.17 h / 20 °C 5: acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 0.92 h / 20 °C 6: sodium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; acetone / 1.5 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: isopropylmagnesium chloride/lithium chloride complex / tetrahydrofuran / 1.08 h / -70 - 20 °C 2: lithium borohydride / tetrahydrofuran / 20 °C 3: hydrogenchloride / tetrahydrofuran; water / 30 h / 90 °C 4: acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 0.92 h / 20 °C 5: sodium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; acetone / 1.17 h / 80 °C / Inert atmosphere; Microwave irradiation | ||
Multi-step reaction with 6 steps 1: isopropylmagnesium chloride/lithium chloride complex / tetrahydrofuran / 1.08 h / -70 - 20 °C 2: lithium borohydride / tetrahydrofuran / 20 °C 3: triethylamine; p-toluenesulfonylanhydride / tetrahydrofuran / 0 - 20 °C 4: trifluoroacetic acid / dichloromethane / 1.17 h / 20 °C 5: acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 0.92 h / 20 °C 6: sodium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; acetone / 1.17 h / 80 °C / Inert atmosphere; Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: isopropylmagnesium chloride/lithium chloride complex / tetrahydrofuran / 1.08 h / -70 - 20 °C 2: lithium borohydride / tetrahydrofuran / 20 °C 3: hydrogenchloride / tetrahydrofuran; water / 30 h / 90 °C 4: acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 0.92 h / 20 °C 5: sodium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; acetone / 1.17 h / 80 °C / Inert atmosphere; Microwave irradiation 6: toluene-4-sulfonic acid / water; acetonitrile / 72 h / 20 °C | ||
Multi-step reaction with 7 steps 1: isopropylmagnesium chloride/lithium chloride complex / tetrahydrofuran / 1.08 h / -70 - 20 °C 2: lithium borohydride / tetrahydrofuran / 20 °C 3: triethylamine; p-toluenesulfonylanhydride / tetrahydrofuran / 0 - 20 °C 4: trifluoroacetic acid / dichloromethane / 1.17 h / 20 °C 5: acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 0.92 h / 20 °C 6: sodium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; acetone / 1.17 h / 80 °C / Inert atmosphere; Microwave irradiation 7: toluene-4-sulfonic acid / water; acetonitrile / 72 h / 20 °C | ||
Multi-step reaction with 8 steps 1: isopropylmagnesium chloride/lithium chloride complex / tetrahydrofuran / 1.08 h / -70 - 20 °C 2: lithium borohydride / tetrahydrofuran / 20 °C 3: hydrogenchloride / tetrahydrofuran; water / 30 h / 90 °C 4: acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 0.92 h / 20 °C 5: dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate / water; acetone / 0.75 h / 80 °C / Inert atmosphere; Microwave irradiation 6: Burgess Reagent / dichloromethane / 0.67 h / 29 °C 7: toluene-4-sulfonic acid / water; acetonitrile / 20 °C 8: 4-methyl-morpholine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / N,N-dimethyl-formamide / 2.5 h / 20 °C |
Multi-step reaction with 9 steps 1: isopropylmagnesium chloride/lithium chloride complex / tetrahydrofuran / 1.08 h / -70 - 20 °C 2: lithium borohydride / tetrahydrofuran / 20 °C 3: triethylamine; p-toluenesulfonylanhydride / tetrahydrofuran / 0 - 20 °C 4: trifluoroacetic acid / dichloromethane / 1.17 h / 20 °C 5: acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 0.92 h / 20 °C 6: dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate / water; acetone / 0.75 h / 80 °C / Inert atmosphere; Microwave irradiation 7: Burgess Reagent / dichloromethane / 0.67 h / 29 °C 8: toluene-4-sulfonic acid / water; acetonitrile / 20 °C 9: 4-methyl-morpholine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / N,N-dimethyl-formamide / 2.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: isopropylmagnesium chloride/lithium chloride complex / tetrahydrofuran / 1.08 h / -70 - 20 °C 2: lithium borohydride / tetrahydrofuran / 20 °C 3: hydrogenchloride / tetrahydrofuran; water / 30 h / 90 °C 4: acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 0.92 h / 20 °C 5: dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate / water; acetone / 0.75 h / 80 °C / Inert atmosphere; Microwave irradiation | ||
Multi-step reaction with 6 steps 1: isopropylmagnesium chloride/lithium chloride complex / tetrahydrofuran / 1.08 h / -70 - 20 °C 2: lithium borohydride / tetrahydrofuran / 20 °C 3: triethylamine; p-toluenesulfonylanhydride / tetrahydrofuran / 0 - 20 °C 4: trifluoroacetic acid / dichloromethane / 1.17 h / 20 °C 5: acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 0.92 h / 20 °C 6: dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate / water; acetone / 0.75 h / 80 °C / Inert atmosphere; Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: isopropylmagnesium chloride/lithium chloride complex / tetrahydrofuran / 1.08 h / -70 - 20 °C 2: lithium borohydride / tetrahydrofuran / 20 °C 3: hydrogenchloride / tetrahydrofuran; water / 30 h / 90 °C 4: acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 0.92 h / 20 °C 5: dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate / water; acetone / 0.75 h / 80 °C / Inert atmosphere; Microwave irradiation 6: Burgess Reagent / dichloromethane / 0.67 h / 29 °C 7: toluene-4-sulfonic acid / water; acetonitrile / 20 °C | ||
Multi-step reaction with 8 steps 1: isopropylmagnesium chloride/lithium chloride complex / tetrahydrofuran / 1.08 h / -70 - 20 °C 2: lithium borohydride / tetrahydrofuran / 20 °C 3: triethylamine; p-toluenesulfonylanhydride / tetrahydrofuran / 0 - 20 °C 4: trifluoroacetic acid / dichloromethane / 1.17 h / 20 °C 5: acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 0.92 h / 20 °C 6: dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate / water; acetone / 0.75 h / 80 °C / Inert atmosphere; Microwave irradiation 7: Burgess Reagent / dichloromethane / 0.67 h / 29 °C 8: toluene-4-sulfonic acid / water; acetonitrile / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: isopropylmagnesium chloride/lithium chloride complex / tetrahydrofuran / 1.08 h / -70 - 20 °C 2: lithium borohydride / tetrahydrofuran / 20 °C 3: hydrogenchloride / tetrahydrofuran; water / 30 h / 90 °C | ||
Multi-step reaction with 4 steps 1: isopropylmagnesium chloride/lithium chloride complex / tetrahydrofuran / 1.08 h / -70 - 20 °C 2: lithium borohydride / tetrahydrofuran / 20 °C 3: triethylamine; p-toluenesulfonylanhydride / tetrahydrofuran / 0 - 20 °C 4: trifluoroacetic acid / dichloromethane / 1.17 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: isopropylmagnesium chloride/lithium chloride complex / tetrahydrofuran / 1.08 h / -70 - 20 °C 2: lithium borohydride / tetrahydrofuran / 20 °C 3: hydrogenchloride / tetrahydrofuran; water / 30 h / 90 °C 4: acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 0.92 h / 20 °C 5: dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate / water; acetone / 0.75 h / 80 °C / Inert atmosphere; Microwave irradiation 6: Burgess Reagent / dichloromethane / 0.67 h / 29 °C | ||
Multi-step reaction with 7 steps 1: isopropylmagnesium chloride/lithium chloride complex / tetrahydrofuran / 1.08 h / -70 - 20 °C 2: lithium borohydride / tetrahydrofuran / 20 °C 3: triethylamine; p-toluenesulfonylanhydride / tetrahydrofuran / 0 - 20 °C 4: trifluoroacetic acid / dichloromethane / 1.17 h / 20 °C 5: acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 0.92 h / 20 °C 6: dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate / water; acetone / 0.75 h / 80 °C / Inert atmosphere; Microwave irradiation 7: Burgess Reagent / dichloromethane / 0.67 h / 29 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: isopropylmagnesium chloride/lithium chloride complex / tetrahydrofuran / 1.08 h / -70 - 20 °C 2: lithium borohydride / tetrahydrofuran / 20 °C 3: hydrogenchloride / tetrahydrofuran; water / 30 h / 90 °C 4: acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 0.92 h / 20 °C | ||
Multi-step reaction with 5 steps 1: isopropylmagnesium chloride/lithium chloride complex / tetrahydrofuran / 1.08 h / -70 - 20 °C 2: lithium borohydride / tetrahydrofuran / 20 °C 3: triethylamine; p-toluenesulfonylanhydride / tetrahydrofuran / 0 - 20 °C 4: trifluoroacetic acid / dichloromethane / 1.17 h / 20 °C 5: acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 0.92 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With isopropylmagnesium chloride/lithium chloride complex In tetrahydrofuran at -70 - 20℃; for 1.08333h; | 2 Step 2: Synthesis of Intermediate I-7.2 I-7.1 (9.42 g, 27.63 mmol) and tert-butyl 4-oxopiperidine-1-carboxylate (6.24 g, 30.40 mmol) in dry THF (200 mL) is cooled down to -70° C. Isopropylmagnesium chloride-lithium chloride complex (1.3 mol/L in THF, 23.38 mL, 30.40 mmol) is added dropwise and reaction mixture is stirred for further 20 minutes at this temperature, is allowed to come to r.t. and stirred for 45 minutes. The reaction mixture is quenched with water and extracted with ethyl acetate. The organic layer is washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude residue is purified by flash column chromatography (petroleum ether:EtOAc=95:5 to 40:60) to provide I-7.2. Yield 74%, m/z 326,328 [M+H-tert-Bu]+, rt 1.09 min, LC-MS Method Z011_S03. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sulfuric acid; In water; at 80℃; for 1.5h; | To <strong>[1133123-02-0]4-bromo-2-iodobenzoic acid</strong> (9.0 g, 27.53 mmol) in methanol (50 mL) is added concentrated sulphuric acid (10 mL) and the reaction mixture is stirred for 90 minutes at 80 C. The reaction mixture is poured onto ice water, sodium hydrogen carbonate is added until a pH value of 7 is reached and the reaction mixture is extracted with ethyl acetate. The organic layer is washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Yield 95%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 80℃; | 8 Preparation of Compound 105-3 Compound 21-4 5g (28.90mmol), methyl 4-bromo-2-iodo-benzoate (methyl 4-bromo-2-iodobenzoate) 10.84g (31.79mmol), Pd (pph3) 43.34g (2.89mmol), Insert the K2CO3 11.98g (86.71mmol) into toluene, H2O, by ethanol 60mL, 12mL, 12mL wasrefluxed at 80 ° C. Ethyl acetate (Ethyl acetate) and was extracted with distilled water,to remove water and to give the title compound 105-3 8.11g (82%) was purified by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane Reflux; | 1 [Synthesis of 1-1`] Round bottom flask was charged with (1-phenyl-1H-indol-3-yl) boronic acid 83.70 g, methyl 4-bromo-2-iodobenzoate 100 g of 1,4-Dioxane was dissolved in 1200 ml K2CO3 (2M) and 450 ml Pd (PPh3) 4 was put 10.2 g was stirred under reflux. Check the reaction by TLC and the reaction was terminated after addition of water. After purification the organic layer was extracted with EA and filtered under reduced pressure to give the intermediate column 1-1` 93.2 g (yield: 78%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene Reflux; | Synthesis of A1-3 6.5 g of intermediate A1-2, methyl 4-bromo-2-iodobenzoate 11.7 g,4.5 g of t-BuONa, 1.2 g of Pd2(dba) 3, (t-Bu)3P 1.5 ml were dissolved in 150 ml of toluene, and the mixture was stirred under reflux. After completion of the reaction was confirmed by TLC, the organic layer was extracted with MC,After pressure filtration, the column was purified to obtain 8.83 g (yield 67%) of Intermediate A1-3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper(l) iodide; caesium carbonate / toluene / 16 h / 130 °C / Inert atmosphere 2: water; sodium hydroxide / methanol / 12 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper(l) iodide; caesium carbonate / toluene / 16 h / 130 °C / Inert atmosphere 2: water; sodium hydroxide / methanol / 12 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: copper(l) iodide; caesium carbonate / toluene / 16 h / 130 °C / Inert atmosphere 2: water; sodium hydroxide / methanol / 12 h / Reflux 3: 9-(2-mesityl)-10-methylacridinium perchlorate; sodium carbonate / water; acetonitrile / 16 h / 20 °C / Irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: copper(l) iodide; caesium carbonate / toluene / 16 h / 130 °C / Inert atmosphere 2: water; sodium hydroxide / methanol / 12 h / Reflux 3: 9-(2-mesityl)-10-methylacridinium perchlorate; sodium carbonate / water; acetonitrile / 16 h / 20 °C / Irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; caesium carbonate In toluene at 130℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; caesium carbonate In toluene at 130℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride; sodium nitrite / water / 0.67 h / 0 °C / Inert atmosphere 1.2: 2.17 h / 0 - 90 °C / Inert atmosphere 2.1: sulfuric acid / 12 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79.4% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water; toluene for 12h; Reflux; | 1-1 To a 1 L round bottom flask reactor were added 4-bromo-2-iodobenzoate (31.7 g, 93 mmol)Phenylboronic acid (20 g, 164 mmol),Potassium carbonate (26.4 g, 191 mmol),Tetrakis triphenylphosphine palladium (2.2 g, 2 mmol),80 mL of water, 150 mL of toluene and 150 mL of 1,4-dioxane are added, and the mixture is refluxed and stirred for 12 hours.After completion of the reaction, the reaction product was separated, and the organic layer was concentrated under reduced pressure. The resultant product was separated by column chromatography to obtain (21.5 g, 79.4%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diisobutylaluminium hydride In toluene at -78℃; for 2.5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: diisobutylaluminium hydride / toluene / 2.5 h / -78 °C / Inert atmosphere 2: silica gel; pyridinium chlorochromate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 3: triphenylphosphine / 1-methyl-pyrrolidin-2-one / 0.17 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: diisobutylaluminium hydride / toluene / 2.5 h / -78 °C / Inert atmosphere 2: silica gel; pyridinium chlorochromate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 3: triphenylphosphine / 1-methyl-pyrrolidin-2-one / 0.17 h / 100 °C / Inert atmosphere 4: dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; silver fluoride; dichloro(1,5-cyclooctadiene)palladium(II) / 1,4-dioxane / 12 h / 80 °C / Schlenk technique; Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: diisobutylaluminium hydride / toluene / 2.5 h / -78 °C / Inert atmosphere 2: silica gel; pyridinium chlorochromate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With N,N,N,N,-tetramethylethylenediamine; potassium carbonate In dimethyl sulfoxide at 20℃; Inert atmosphere; Irradiation; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: methyl 4-bromo-2-iodobenzoate; C24H24BO3P With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water Stage #2: methylmagnesium bromide In tetrahydrofuran Stage #3: With hydrogenchloride; acetic acid In water | 9.1; 9.2; 9.3 1) Synthesis of Intermediate 43-1 Intermediate 1-2 reacted with methyl 4-bromo-2-iodobenzoate (CAS: 1093418-75-7) and potassium carbonate under a palladium catalyst to synthesize Intermediate 43-1. Intermediate 43-1 was confirmed by LC-MS. C26H18BrO3P: M+1 489.69. 2) Synthesis of Intermediate 43-2 (0464) Intermediate 43-1 reacted with a methyl magnesium bromide solution to synthesize Intermediate 43-2. Intermediate 43-2 was confirmed by LC-MS. (0465) C27H22BrO2P: M+1 489.60. (0466) 3) Synthesis of Intermediate 43-3 (0467) Intermediate 43-2 reacted under a hydrochloric acid catalyst to synthesize Intermediate 43-3. Intermediate 43-3 was confirmed by LC-MS. (0468) C27H20BrOP: M+1 471.34. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 10h; Heating; | 1 Compounds A1 to A10 of Table 1 below were prepared using the reaction of any one of Steps 1-1 to 1-4. General procedure: As a reactant, 1eq SM1 (boronic acid derivative) and 1.05eq SM2 (halogen-substituted compound) were added to tetrahydrofuran, followed by 2M potassium carbonate aqueous solution (30 vol. Ratio to THF).Tetrakistriphenyl-phosphinopalladium (2 mol%) was added thereto, followed by heating and stirring for 10 hours. After the temperature was lowered to room temperature and the reaction was terminated, the aqueous solution of potassium carbonate was removed to separate the layers. Compounds A1 to A10 were prepared by vacuum distillation after removal of the solvent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,2-dimethoxyethane; water at 110℃; for 0.75h; Inert atmosphere; Microbiological reaction; | Methyl 2',5,6'-trimethoxy-4'-(2-methyloctan-2-yl)-[1,10-biphenyl]-2-carboxylate(15) General procedure: Argon was bubbledthrough a mixture of boronic acid 13 [27] (1.43 g, 4.65 mmol), methyl 2-bromo-4-methoxybenzoate (14, 950mg, 3.88 mmol), and Cs2CO3 (5.06 g, 15.5 mmol) in DME/H2O (5:1, 10.5 mL of DME and 2.1 mL ofH2O) for 10 min. The Pd(PPh3)4 (448 mg, 0.39 mmol) catalyst was added to the mixture while argonbubbling was maintained through the mixture, and degassing was continued for an additional 5 min.The reaction mixture was microwaved with stirring at 110 C for 45 min in a Biotage apparatus [25].Then, the mixture was cooled to room temperature and filtered through a short celite pad. Volatileswere removed under reduced pressure, and Et2O was added. The ethereal solution was washed withwater and brine, dried over MgSO4, and concentrated under reduced pressure. Purification by flashcolumn chromatography on silica gel (10-30% EtOAc/hexane) gave 15 (1.4 g, 84% yield) as a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 0.75 h / 110 °C / Inert atmosphere; Microbiological reaction 2: 9-iodo-9-borabicyclo{3.3.1}nonane / dichloromethane / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 0.75 h / 110 °C / Inert atmosphere; Microbiological reaction 2.1: 9-iodo-9-borabicyclo{3.3.1}nonane / dichloromethane / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 0 °C / Inert atmosphere 3.2: 1.5 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 0.75 h / 110 °C / Inert atmosphere; Microbiological reaction 2.1: 9-iodo-9-borabicyclo{3.3.1}nonane / dichloromethane / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 0 °C / Inert atmosphere 3.2: 1.5 h / 0 - 20 °C / Inert atmosphere 4.1: triethylamine; 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) / isopropyl alcohol / 24 h / 75 °C / Inert atmosphere; Sealed tube 4.2: 3 h / 20 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 0.75 h / 110 °C / Inert atmosphere; Microbiological reaction 2.1: 9-iodo-9-borabicyclo{3.3.1}nonane / dichloromethane / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 0 °C / Inert atmosphere 3.2: 1.5 h / 0 - 20 °C / Inert atmosphere 4.1: triethylamine; 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) / isopropyl alcohol / 24 h / 75 °C / Inert atmosphere; Sealed tube 4.2: 3 h / 20 °C / Inert atmosphere; Sealed tube 5.1: scandium tris(trifluoromethanesulfonate) / acetonitrile; ethanol / 8 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | With tert.-butylhydroperoxide; palladium diacetate; silver(l) oxide In water at 120℃; for 12h; Sealed tube; | 19.A Step A. Methyl 4-bromo-2-isobutyrylbenzoate To a tube charged with methyl 4-bromo-2- iodobenzoate (1420 mg, 4.2 mmol) was added isobutyraldehyde (1201 mg, 17 mmol), Pd(OAc)2(94 mg, 0.4 mmol), Ag2O (1255 mg, 5.4 mmol) and an aqueous solution (70% w/w) of tert-butyl hydroperoxide (TBHP) (2681 mg, 21 mmol). The reaction mixture was degassed with nitrogen, sealed and heated with stirring at 120 C for 12 h. The reaction was cooled to room temperature, diluted with aqueous NaHCO3solution (50 mL) and extracted with ethyl acetate (100 mLx2). The combined organic extract washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by silica column chromatography (gradient elution: 10- 30% EtOAc in heptane) to give the title compound as a white solid (167 mg, yield: 14%). LCMS (ES-API): mass calcd. for C12H13BrO3, 284.0; m/z found, 285.0 [M+H]+.1H NMR (400 MHz, CDCl3) d 7.83 (d, J = 8.31 Hz, 1H), 7.62 (dd, J = 1.96, 8.31 Hz, 1H), 7.42 (d, J = 1.96 Hz, 1H), 3.88 (s, 3H), 3.02 (spt, J = 6.89 Hz, 1H), 1.21 (d, J = 6.89 Hz, 6H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70.3% | With 3,6-dioxa-1,8-diaminooctane; palladium diacetate; sodium carbonate; tris-(o-tolyl)phosphine In water for 15h; Inert atmosphere; Reflux; | 4.1 The synthesis method of compound 1-a is as follows: S1: Under the protection of nitrogen, compound A (5g, 212.01g/mol, 23.58mmol), Compound 1-e (1.1eq, 8.84g, 340.94g/mol, 25.94mmol) and sodium carbonate (2eq, 5g, 105.99g/mol, 47.16mmol) were added to ethylene glycol diamine ether (100g, 20 of compound A times the mass) and water (100g, 20 times the mass of compound A), After stirring and mixing, add tris(o-tolyl)phosphine (0.05eq, 0.36g, 304.37g/mol, 1.18mmol) and palladium(II) acetate (0.01eq, 0.05g, 224.51g/mol, 0.24mmol) , After heating to reflux for 15h, The organic phase was separated, washed with water, dried over anhydrous magnesium sulfate, and spin-dried to obtain a crude product. After the crude product was subjected to column chromatography, compound C (6.32g, yield 70.3%) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; | A Synthesis of methyl 4-bromo-2-iodobenzoate I-1011 Cesium carbonate [534-17-8] (5.98 g, 18.35 mmol) and methyl iodide [74-88-4] (1.14 mL, 2.28 g/mL 1 l ddd i d l i f 4b 2 iodobenzoic ac reaction mixtu organic layer was concentrated in vacuo. The crude was purified by flash column 10 chromatography (silica; EtOAc in Heptane from 0/100 to 20/80). The desired fractions were collected and concentrated in vacuo to yield methyl 4-bromo-2-iodobenzoate I- 1011 (4.27 g, 80%) as a colorless oil |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Stage #1: methyl 4-bromo-2-iodobenzoate; isopropylmagnesium chloride In tetrahydrofuran at -78 - 0℃; for 0.5h; Inert atmosphere; Stage #2: With zinc dibromide In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere; Stage #3: Benzyloxyacetyl chloride With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 60℃; for 2h; Inert atmosphere; | A Synthesis of methyl 2-(2-(benzyloxy)acetyl)-4-bromobenzoate I-1012 Isopropylmagnes was added drop15 1.47 mmol) in T at 0C for 30 mi 8] (367 mg, 1.61 min. 2-(Benzyloxy)acetyl chloride I-1009 (325 mg, 1.76 mmol) and tetrakis(triphenylphosphine)palladium (0) [14221-01-3] (86 mg, 0.073 mmol) were 20 added and the resulting mixture was stirred at 60C for 2h under nitrogen atmosphere. The reaction mixture was diluted with sat. aqueous NH4Cl and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; DCM in heptane 0/100 to 100/0). The desired fractions were collected and concentrated 25 in vacuo to yield methyl 2-(2-(benzyloxy)acetyl)-4-bromobenzoate I-1012 (468 mg, 82%) as a yellow sticky solid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: isopropylmagnesium chloride lithium chloride / tetrahydrofuran / 0.5 h / -78 °C 1.2: 2 h / -78 - 20 °C 2.1: hydrazine hydrate monohydrate / ethanol / 85 °C 3.1: trichlorophosphate / 1.5 h / 100 °C 4.1: ethanol / 120 h / 85 °C 5.1: palladium diacetate; dicyclohexyl(2’,4’,6’-triisopropyl-[ 1,1’-bi-phenyl]-2-yl)phosphane; anhydrous potassium acetate / 1,4-dioxane / 90 °C / Inert atmosphere 6.1: anhydrous sodium carbonate; dichloro[ 1,1’-bis(di-tert-butylphosphino)ferrocene]palladium (II) / water monomer; 1,2-dimethoxyethane / 6 h / 80 °C / Inert atmosphere | ||
Multi-step reaction with 6 steps 1.1: isopropylmagnesium chloride lithium chloride / tetrahydrofuran / 0.5 h / -78 °C 1.2: 2 h / -78 - 20 °C 2.1: hydrazine hydrate monohydrate / ethanol / 85 °C 3.1: trichlorophosphate / 1.5 h / 100 °C 4.1: ethanol / 120 h / 85 °C 5.1: palladium diacetate; dicyclohexyl(2’,4’,6’-triisopropyl-[ 1,1’-bi-phenyl]-2-yl)phosphane; anhydrous potassium acetate / 1,4-dioxane / 90 °C / Inert atmosphere 6.1: anhydrous sodium carbonate; dichloro[ 1,1’-bis(di-tert-butylphosphino)ferrocene]palladium (II) / water monomer; 1,2-dimethoxyethane / 6 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: isopropylmagnesium chloride lithium chloride / tetrahydrofuran / 0.5 h / -78 °C 1.2: 2 h / -78 - 20 °C 2.1: hydrazine hydrate monohydrate / ethanol / 85 °C 3.1: trichlorophosphate / 1.5 h / 100 °C 4.1: ethanol / 120 h / 85 °C 5.1: palladium diacetate; dicyclohexyl(2’,4’,6’-triisopropyl-[ 1,1’-bi-phenyl]-2-yl)phosphane; anhydrous potassium acetate / 1,4-dioxane / 90 °C / Inert atmosphere 6.1: anhydrous sodium carbonate; dichloro[ 1,1’-bis(di-tert-butylphosphino)ferrocene]palladium (II) / water monomer; 1,2-dimethoxyethane / 6 h / 80 °C 7.1: palladium diacetate; dicyclohexyl(2’,4’,6’-triisopropyl-[ 1,1’-bi-phenyl]-2-yl)phosphane; anhydrous potassium acetate / 1,4-dioxane / 18 h / 90 °C / Inert atmosphere | ||
Multi-step reaction with 7 steps 1.1: isopropylmagnesium chloride lithium chloride / tetrahydrofuran / 0.5 h / -78 °C 1.2: 2 h / -78 - 20 °C 2.1: hydrazine hydrate monohydrate / ethanol / 85 °C 3.1: trichlorophosphate / 1.5 h / 100 °C 4.1: ethanol / 120 h / 85 °C 5.1: palladium diacetate; dicyclohexyl(2’,4’,6’-triisopropyl-[ 1,1’-bi-phenyl]-2-yl)phosphane; anhydrous potassium acetate / 1,4-dioxane / 90 °C / Inert atmosphere 6.1: anhydrous sodium carbonate; dichloro[ 1,1’-bis(di-tert-butylphosphino)ferrocene]palladium (II) / water monomer; 1,2-dimethoxyethane / 6 h / 80 °C 7.1: palladium diacetate; dicyclohexyl(2’,4’,6’-triisopropyl-[ 1,1’-bi-phenyl]-2-yl)phosphane; anhydrous potassium acetate; 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4',4',5',5'-tetramethyl-1,3,2-dioxaborolane / 1,4-dioxane / 18 h / 90 °C / Inert atmosphere 7.2: 20 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.92% | Stage #1: methyl 4-bromo-2-iodobenzoate With isopropylmagnesium chloride lithium chloride In tetrahydrofuran at -78℃; for 0.5h; Stage #2: acetic anhydride In tetrahydrofuran at -78 - 20℃; for 2h; | 172 A 2.0M solution of isopropylmagnesium chloride in THF (35.19 mL, 70.37 mmol) was added dropwise at -78°C to a solution of methyl 4-bromo-2-iodobenzoate (21.81 g, 63.98 mmol) in THF (221.7 mL). After 30 minutes acetic acid acetyl ester (7.86 mL, 83.17 mmol) was added at the same temperature. After addition was complete, the reaction mixture was stirred at room temperature for 2 hours then it was quenched with a saturated aqueous solution of ammonium chloride and extracted three times with EtOAc. The combined organic phases were washed with brine, filtered and evaporated in vacuo. The residue was purified by column chromatography (KP-Sil silica gel, SNAP 750) eluting with a gradient of EtOAc in cyclohexane from 5% to 25% to give methyl 2-acetyl-4-bromobenzoate (13.8 g, 53.69 mmol, 83.92% yield) as a yellowish oil.1H NMR (400 MHz, DMSO-d6) ^ 2.52 (s, 3 H), 3.81 (s, 3 H), 7.72 - 7.76 (m, 1 H), 7.82 - 7.86 (m, 1 H), 7.88 (d, J = 1.76 Hz, 1 H). LC-MS (Method A): r.t. 0.98 min, MS (ESI) m/z = 257.14 and 259.07 [M+H]+. |
83.92% | Stage #1: methyl 4-bromo-2-iodobenzoate With isopropylmagnesium chloride lithium chloride In tetrahydrofuran at -78℃; for 0.5h; Stage #2: acetic anhydride In tetrahydrofuran at -78 - 20℃; for 2h; | 172 A 2.0M solution of isopropylmagnesium chloride in THF (35.19 mL, 70.37 mmol) was added dropwise at -78°C to a solution of methyl 4-bromo-2-iodobenzoate (21.81 g, 63.98 mmol) in THF (221.7 mL). After 30 minutes acetic acid acetyl ester (7.86 mL, 83.17 mmol) was added at the same temperature. After addition was complete, the reaction mixture was stirred at room temperature for 2 hours then it was quenched with a saturated aqueous solution of ammonium chloride and extracted three times with EtOAc. The combined organic phases were washed with brine, filtered and evaporated in vacuo. The residue was purified by column chromatography (KP-Sil silica gel, SNAP 750) eluting with a gradient of EtOAc in cyclohexane from 5% to 25% to give methyl 2-acetyl-4-bromobenzoate (13.8 g, 53.69 mmol, 83.92% yield) as a yellowish oil.1H NMR (400 MHz, DMSO-d6) ^ 2.52 (s, 3 H), 3.81 (s, 3 H), 7.72 - 7.76 (m, 1 H), 7.82 - 7.86 (m, 1 H), 7.88 (d, J = 1.76 Hz, 1 H). LC-MS (Method A): r.t. 0.98 min, MS (ESI) m/z = 257.14 and 259.07 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.66% | Stage #1: methyl 4-bromo-2-iodobenzoate With isopropylmagnesium chloride lithium chloride In tetrahydrofuran at -78℃; for 0.25h; Stage #2: 2-Methylpropionic anhydride In tetrahydrofuran at -78 - 20℃; for 2h; | 172 To a solution of methyl 4-bromo-2-iodobenzoate (1.0 g, 2.93 mmol) in THF (10 mL) cooled to -78°C, a 2.0M solution of isopropyl magnesium chloride in THF (1.61 mL, 3.23 mmol) was added. After 15 minutes, 2-methylpropanoic acid (2-methyl-1-oxopropyl) ester (0.63 mL, 3.81 mmol) was added dropwise at the same temperature and then the reaction mixture was stirred at room temperature for 2 h. The mixture was quenched with saturated ammonium chloride solution and extracted three times with EtOAc. The combined organic phases were washed with brine, filtered and evaporated in vacuo. The residue was purified by column chromatography (KP-Sil, SNAP 50g) eluting with a gradient of EtOAc in cyclohexane from 0% to 20% to give methyl 4-bromo-2-(2-methylpropanoyl)benzoate (800 mg, 2.806 mmol, 95.66% yield) as a white solid.1H NMR (400 MHz, DMSO-d6) δ 1.08 (d, J = 6.89 Hz, 6H), 3.13 (hept, J = 6.89 Hz, 1H), 3.79 (s, 3H), 7.74 (dd, J = 1.75, 0.67 Hz, 1H), 7.80 - 7.82 (m, 2H). LC-MS (Method A): r.t.1.16 min, MS (ESI) m/z = 285.1 and 287.1 [M+H]+. |
95.66% | Stage #1: methyl 4-bromo-2-iodobenzoate With isopropylmagnesium chloride lithium chloride In tetrahydrofuran at -78℃; for 0.25h; Stage #2: 2-Methylpropionic anhydride In tetrahydrofuran at -78 - 20℃; for 2h; | 172 To a solution of methyl 4-bromo-2-iodobenzoate (1.0 g, 2.93 mmol) in THF (10 mL) cooled to -78°C, a 2.0M solution of isopropyl magnesium chloride in THF (1.61 mL, 3.23 mmol) was added. After 15 minutes, 2-methylpropanoic acid (2-methyl-1-oxopropyl) ester (0.63 mL, 3.81 mmol) was added dropwise at the same temperature and then the reaction mixture was stirred at room temperature for 2 h. The mixture was quenched with saturated ammonium chloride solution and extracted three times with EtOAc. The combined organic phases were washed with brine, filtered and evaporated in vacuo. The residue was purified by column chromatography (KP-Sil, SNAP 50g) eluting with a gradient of EtOAc in cyclohexane from 0% to 20% to give methyl 4-bromo-2-(2-methylpropanoyl)benzoate (800 mg, 2.806 mmol, 95.66% yield) as a white solid.1H NMR (400 MHz, DMSO-d6) δ 1.08 (d, J = 6.89 Hz, 6H), 3.13 (hept, J = 6.89 Hz, 1H), 3.79 (s, 3H), 7.74 (dd, J = 1.75, 0.67 Hz, 1H), 7.80 - 7.82 (m, 2H). LC-MS (Method A): r.t.1.16 min, MS (ESI) m/z = 285.1 and 287.1 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.39% | Stage #1: methyl 4-bromo-2-iodobenzoate With isopropylmagnesium chloride lithium chloride In tetrahydrofuran at -78℃; for 0.5h; Stage #2: cyclopropanecarbonyl cyclopropanecarboxylate In tetrahydrofuran at -78 - 20℃; for 2h; | 172 To a solution of methyl 4-bromo-2-iodobenzoate (1.6 g, 4.69 mmol) in THF (16.26 mL), a 2 M solution of isopropylmagnesium chloride in THF (2.58 mL, 5.16 mmol) was added dropwise at -78°C. After 30 minutes cyclopropanecarboxylic anhydride (0.67 mL, 6.1 mmol) was added at the same temperature. After addition was complete the reaction mixture was stirred at room temperature for 2 hours. It was then quenched with a saturated solution of ammonium chloride and extracted three times with EtOAc. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (KP silica gel, SNAP 340) eluting with a gradient of EtOAc in cyclohexane from 2% to 40% to give methyl 4-bromo-2-(cyclopropanecarbonyl)benzoate (1.108 g, 3.914 mmol, 83.39% yield) as a yellow oil.1H NMR (400 MHz, DMSO-d6) δ 1.05 - 1.14 (m, 4H), 2.40 (tt, J = 6.7, 5.5 Hz, 1H), 3.80 (s, 3H), 7.76 (dd, J = 8.2, 0.5 Hz, 1H), 7.80 - 7.89 (m, 2H). LC-MS (Method A): r.t.1.08 min. MS (ESI) m/z of product not observed due to poor ionization |
83.39% | Stage #1: methyl 4-bromo-2-iodobenzoate With isopropylmagnesium chloride lithium chloride In tetrahydrofuran at -78℃; for 0.5h; Stage #2: cyclopropanecarbonyl cyclopropanecarboxylate In tetrahydrofuran at -78 - 20℃; for 2h; | 172 To a solution of methyl 4-bromo-2-iodobenzoate (1.6 g, 4.69 mmol) in THF (16.26 mL), a 2 M solution of isopropylmagnesium chloride in THF (2.58 mL, 5.16 mmol) was added dropwise at -78°C. After 30 minutes cyclopropanecarboxylic anhydride (0.67 mL, 6.1 mmol) was added at the same temperature. After addition was complete the reaction mixture was stirred at room temperature for 2 hours. It was then quenched with a saturated solution of ammonium chloride and extracted three times with EtOAc. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (KP silica gel, SNAP 340) eluting with a gradient of EtOAc in cyclohexane from 2% to 40% to give methyl 4-bromo-2-(cyclopropanecarbonyl)benzoate (1.108 g, 3.914 mmol, 83.39% yield) as a yellow oil.1H NMR (400 MHz, DMSO-d6) δ 1.05 - 1.14 (m, 4H), 2.40 (tt, J = 6.7, 5.5 Hz, 1H), 3.80 (s, 3H), 7.76 (dd, J = 8.2, 0.5 Hz, 1H), 7.80 - 7.89 (m, 2H). LC-MS (Method A): r.t.1.08 min. MS (ESI) m/z of product not observed due to poor ionization |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; caesium fluoride In 1,4-dioxane at 100℃; for 6h; Inert atmosphere; | 100 Methyl 2-(6-cyclopropyl-5-fluoro-1-oxo-spiro[3H-isoquinoline-4,1'-cyclopropane]-2- yl)acetate: To a solution of methyl 2-(6-bromo-5-fluoro-1-oxo-spiro[3H-isoquinoline-4,1'- cyclopropane]-2-yl)acetate (200 mg, 0.61 mmol) and cyclopropylboronic acid (151 mg, 1.75 mmol) in 1,4-dioxane (2.0 mL) were added CsF (266 mg, 1.75 mmol) and Pd(dppf)Cl2 (43 mg, 0.06 mmol). The reaction mixture was stirred at 100 °C for 6 h. The reaction mixture was diluted with water (20 mL) and extracted with EtOAc (3 × 10 mL). The combined organics were washed with brine (10 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography.1H NMR (400 MHz, CDCl3): δ 7.84 (d, J = 8.0 Hz, 1H), 6.84-6.67 (m, 1H), 4.29 (s, 2H), 3.76 (s, 3H), 3.32 (s, 2H), 2.12-2.05 (m, 1H), 1.67-1.61 (m, 2H), 1.06-0.99 (m, 2H), 0.99-0.93 (m, 2H), 0.78-0.71 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; caesium fluoride In 1,4-dioxane at 90℃; for 16h; Inert atmosphere; | Methyl 4-bromo-2-vinylbenzoate To a mixture of methyl 4-bromo-2-iodo-benzoate (6.0 g, 17.6 mmol), potassium vinyltrifluoroborate (2.4 g, 17.6 mmol), and CsF (8.0 g, 52.8 mmol) in 1,4- dioxane (100 mL) was added Pd(dppf)Cl2 (1.3 g, 1.76 mmol). The reaction mixture was stirred at 90 °C for 16 h. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography.1H NMR (400 MHz, CDCl3): δ 7.77 (d, J = 8.4 Hz, 1H), 7.72 (d, J = 2.0 Hz, 1H), 7.49-7.37 (m, 2H), 5.66 (d, J = 17.2 Hz, 1H), 5.41 (d, J = 10.8 Hz, 1H), 3.90 (s, 3H). |
Tags: 1093418-75-7 synthesis path| 1093418-75-7 SDS| 1093418-75-7 COA| 1093418-75-7 purity| 1093418-75-7 application| 1093418-75-7 NMR| 1093418-75-7 COA| 1093418-75-7 structure
[ 1263376-81-3 ]
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