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CAS No. : | 55552-70-0 | MDL No. : | MFCD01319007 |
Formula : | C4H5BO3 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | CYEFKCRAAGLNHW-UHFFFAOYSA-N |
M.W : | 111.89 | Pubchem ID : | 2734358 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2-[1-(3-Nitrophenyl)ethylamino]-4-[benzimidazol-1-yl]-6-(furan-3-yl)pyrimidine The title compound was prepared from 2-[1-(3-nitrophenyl)ethylamino]-4-[benzimidazol-1-yl]-6-chloropyrimidine and furan-3-boronic acid according to the precedure described in EXAMPLE 306, Step C and using [1,1'-bis(diphenylphosphino)ferrocene]-dichloropalladium(H) as catalyst. Mass spectrum (CH3CN/TFA/NH4O2CH/ESI) 427.0 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 150℃; for 0.333333h;Inert atmosphere; Microwave irradiation; | (step 2) To a mixed solution of the compound (0.300 g) obtained in step 1, 3-furylboronic acid (0.187 g) and potassium carbonate (0.154 g) in DME/water (6 mL)/0.6 mL) was added under an argon atmosphere tetrakis(triphenylphosphine)palladium (0) (Pd(PPh3)4) (0.129 g), and the reaction vessel was irradiated in a microwave reaction apparatus at 150C for 20 min. To the reaction solution was added water, and the resulting product was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (solvent gradient: 0?30% ethyl acetate/hexane) to give tert-butyl 2-(3-furyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate (0.310 g, 92%) as an oil. 1H-NMR(CDCl3):delta1.50(9H,s), 2.95-3.05(2H,m), 3.73-3.77(2H,m), 4.58(2H,s), 6.87(1H,dd,J=1.7Hz,0.7Hz), 7.29(1H,d,J=8.2Hz), 7.39(1H,d,J=8.2Hz), 7.47(1H,dd,J=1.7Hz,1.7Hz), 7.99(1H,s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 100℃;Inert atmosphere; | Step 1: 3-(4-Bromo-3,5-dimethylphenyl)furan A mixture of <strong>[100189-84-2]2,5-dibromo-1,3-dimethylbenzene</strong> (2.00 g), 1-furan-3-ylboronic acid (856 mg), and 2 M aqueous Na2CO3 solution (11 mL) in 1,4-dioxane (40 mL) is purged with argon for 5 min. Tetrakis-triphenylphosphine-palladium-(0) (270 mg) is added and the mixture is stirred at 100 C. over night. More tetrakis-triphenylphosphine-palladium-(0) (50 mg) is added and the mixture is stirred for another 5 h at 100 C. After cooling to room temperature the mixture is diluted with ethyl acetate and aqueous NH4Cl solution. The aqueous phase is extracted with ethyl acetate and the combined extracts are washed with brine, dried over MgSO4 and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 100:0?90:10) to give the title compound. LC (method 7): tR=1.22 min; Mass spectrum (EI+): m/z=250 [M]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.8% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; at 80℃; for 6h;Inert atmosphere; | A solution of fert-butyl 4-bromo-lH-indole-l-carboxylate (LXXI) (10 g, 33.8 mmol), 3-furylboronic acid (LXXII) (5.29 g, 47.3 mmol), K3P04 (14.3 g, 67.5 mmol) and Pd(dppf)Cl2 (1.24 g, 1.69 mmol) in dioxane (150 mL) was heated to 80C for 6 hours under N2. The mixture was filtered and the filtrate was concentrated, the residue was purified by MPLC (PE:EtOAc = 10: 1) to give fert-butyl 4-(furan-3-yl)-lH-indole-l-carboxylate (LXXIII) (8.4 g, 29.6 mmol, 87.8% yield) as yellow oil. NMR (CDC13, 400 MHz) delta ppm 1.70 (s, 9H), 6.7 - 6.81 (m, 2H), 7.28 - 7.38 (m, 2H), 7.56 (d, J=1.6Hz, 1H), 7.66 (d, J=4Hz, 1H), 7.79 (s, 1H), 8.13 (d, J=8Hz, 1H); ESIMS found for Ci7Hi7N03 mlz 284.1 (M+H). |
87.8% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; at 80℃; for 6h;Inert atmosphere; | A solution of fert-butyl 4-bromo-lH-indole-l-carboxylate (LXXXVIII) (10 g, 33.8 mmol), 3-furylboronic acid (LXXXIX) (5.29 g, 47.3 mmol), K3P04 (14.3 g, 67.5 mmol) and Pd(dppf)Cl2 (1.24 g, 1.69 mmol) in dioxane (150 mL) was heated to 80C for 6 h under N2. The mixture was filtered and the filtrate was concentrated, the residue was purified by MPLC (PE:EtOAc = 10: 1) to give fert-butyl 4-(furan-3-yl)-lH-indole-l-carboxylate (XC) (8.4 g, 29.6 mmol, 87.8% yield) as yellow oil. NMR (CDC13, 400 MHz) delta ppm 1.70 (s, 9H), 6.7 - 6.81 (m, 2H), 7.28 - 7.38 (m, 2H), 7.56 (d, J=1.6Hz, 1H), 7.66 (d, J=4Hz, 1H), 7.79 (s, 1H), 8.13 (d, J=8Hz, 1H); ESIMS found for Ci7Hi7N03 mlz 284.1 (M+H). |
87.8% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; at 80℃; for 6h;Inert atmosphere; | A solution of <strong>[676448-17-2]tert-butyl 4-bromo-1H-indole-1-carboxylate</strong> (LXXI) (10 g, 33.8 mmol), 3-furylboronic acid (LXXII) (5.29 g, 47.3 mmol), K3PO4 (14.3 g, 67.5 mmol) and Pd(dppf)Cl2 (1.24 g, 1.69 mmol) in dioxane (150 mL) was heated to 80C for 6 h under N2. The mixture was filtered and the filtrate was concentrated, the residue was purified by MPLC (PE:EtOAc = 10: 1) to give tert-butyl 4-(furan-3-yl)-1H-indole-1-carboxylate (LXXIII) (8.4 g, 29.6 mmol, 87.8% yield) as yellow oil. 1H NMR (CDCI3, 400 MHz) delta ppm 1.70 (s, 9H), 6.7 - 6.81 (m, 2H), 7.28 - 7.38 (m, 2H), 7.56 (d, J=1.6Hz, 1H), 7.66 (d, J=4Hz, 1H), 7.79 (s, 1H), 8.13 (d, J=8Hz, 1H); ESIMS found for C17H17NO3 m/z 284.1 (M+H). |
87.8% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; at 80℃; for 6h;Inert atmosphere; | A solution of <strong>[676448-17-2]tert-butyl 4-bromo-1H-indole-1-carboxylate</strong> (LXXI) (10 g, 33.8 mmol), 3-furylboronic acid (LXXII) (5.29 g, 47.3 mmol), K3P04 (14.3 g, 67.5 mmol) and Pd(dppf)C12 (1.24 g, 1.69 mmol) in dioxane (150 mL) was heated to 80C for 6 h under N2. The mixture was filtered and the filtrate was concentrated, the residue was purified by MPLC (PE:EtOAc = 10:1) to give tert-butyl 4-(furan-3-yl)-1H-indole-1-carboxylate (LXXIII) (8.4 g, 29.6 mmol, 87.8% yield) as yellow oil. ?H NMR (CDC13, 400 MHz) ppm 1.70 (s, 9H), 6.7 - 6.81 (m, 2H), 7.28-7.38 (m, 2H), 7.56 (d,J1.6Hz, 1H), 7.66 (d,J=4Hz, 1H), 7.79 (s, 1H), 8.13 (d,J=8Hz, 1H); ESIMS found for C,7H,7N03 mlz 284.1 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; at 110.0℃; for 3.0h; | General procedure: To an argon degassed solution of 6-halogeno-2,4-dichloropyrido[2,3-d]pyrimidine 6 or 7 (0.5 mmol) in toluene (6mL) the desired (Het)aryl boronic acid was added then (1.5 equiv)potassium carbonate and (0.05 equiv) Pd(PPh3)4 were also added.The reaction was stirred at 110C for the desired time. After completion of the reaction, 10 mL of water was added, and then extracted with dichloromethane (3 10 mL), the organic layers were combined and dried using magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained material was purified on silica gel by column chromatography (CH2Cl2/PE: 90/10)to afford compounds 8-12. 2,4-Dichloro-6-(4-methoxyphenyl)pyrido[2,3-d]pyrimidine (8) (C14H9Cl2N3O): Compound 8 was obtained from 2,4,6-trichloropyrido[2,3-d]pyrimidine 6 using 4-methoxyphenyl boronic acid (1.05 equiv), as a white solid in 83%yield. |
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