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CAS No. : | 1415379-89-3 | MDL No. : | |
Formula : | C16H10N4O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 290.28 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
---|---|---|
85% | With dmap; In dichloromethane; at 20.0℃; for 8.0h;Inert atmosphere; | Di-tert-butyl-dicarbonate ((Boc)2O, 105mg, 0.48mmol) was added to a mixture of DMAP (44mg, 0.36mmol) and compound 5 (87mg, 0.3mmol) in dichloromethane (50mL) at rt. The resulting reaction mixture was stirred for 8h and then was concentrated. The residue was purified by silica gel chromatography using an eluent (2:98 MeOH/CH2Cl2) to afford a yellow solid product 6 (100mg, 85%). Rf=0.77 (1:12 MeOH/CH2Cl2), mp >300C. 1H NMR (CDCl3): δ 1.80 (s, 9H, 3×CH3), 7.70 (dd, J=1.5, 8.0Hz, 1H, Ar-H), 8.14 (d, J=5.5Hz, 1H, Ar-H), 8.22 (d, J=8.5Hz, 1H, Ar-H), 8.32 (dd, J=2.5, 8.5Hz, 1H, Ar-H), 8.39 (dd, J=0.5, 8.5Hz, 1H, Ar-H), 8.69 (d, J=6.0Hz, 1H, Ar-H), 8.70 (s, 1H, Ar-H), 8.97 (dd, J=0.5, 2.0Hz, 1H, Ar-H), 9.34 (s, 1H, Ar-H). MS (ESI): 391 ([M+H]+, 100%). MS (ESI): 413 ([M+Na]+, 20%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; at 100℃; for 20h;Inert atmosphere; | Method B (from 4): A mixture of compound 2 (99mg, 0.4mmol), 4 (184mg, 0.64mmol), Pd(PPh3)4 (46mg, 0.04mmol), and Cs2CO3 (391mg, 1.2mmol) in 1,4-dioxane (100mL) was stirred at 100C under N2 atmosphere for 20h. After cooling to RT, the volatiles were removed under reduced pressure. The residue was purified by silica gel chromatography using an eluent (3:97 MeOH/CH2Cl2) to obtain a yellow solid product 5 (30mg, 26%). Analytical data was identical with Method A. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7% | With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; at 100℃; for 20h;Inert atmosphere; | Method A: A mixture of compound 2 (99mg, 0.4mmol), 2-nitro-5-pyridineboronic acid pinacol ester (160mg, 0.64mmol), Pd(PPh3)4 (46mg, 0.04mmol), and Cs2CO3 (391mg, 1.2mmol) in 1,4-dioxane (100mL) was stirred at 100C under N2 atmosphere for 20h. After cooling to RT, the volatiles were removed under reduced pressure. The residue was purified by silica gel chromatography using an eluent (3:97 MeOH/CH2Cl2) to afford a yellow solid product 5 (8mg, 7%). Rf=0.32 (1:12 MeOH/CH2Cl2), mp >300C. 1H NMR (DMSO-d6): delta 7.52 (d, J=5.5Hz, 1H, Ar-H), 7.76 (dd, J=1.5, 8.0Hz, 1H, Ar-H), 7.98-8.04 (m, 1H, Ar-H), 8.42-8.47 (m, 3H, Ar-H), 8.61 (dd, J=2.5, 8.5Hz, 1H, Ar-H), 9.12 (d, J=2.0Hz, 1H, Ar-H), 9.42 (s, 1H, Ar-H), 11.96 (s, 1H, NH). MS (ESI): 291 ([M+H]+, 100%). MS (ESI): 289 ([M-H]-, 40%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16%; 32% | With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; at 100.0℃; for 20.0h;Inert atmosphere; | General procedure: These two compounds were synthesized from compound 7 and 2-nitro-5-pyridineboronic acid pinacol ester or compound 4 according to the procedure previously described for the synthesis of compound 5. From 2-nitro-5-pyridineboronic acid pinacol ester, yield (5, 10% and 6, 15%); from 4, yield (5, 16% and 6, 32%). Analytical data was identical with that previously described. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10%; 15% | With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; at 100.0℃; for 20.0h;Inert atmosphere; | General procedure: These two compounds were synthesized from compound 7 and 2-nitro-5-pyridineboronic acid pinacol ester or compound 4 according to the procedure previously described for the synthesis of compound 5. From 2-nitro-5-pyridineboronic acid pinacol ester, yield (5, 10% and 6, 15%); from 4, yield (5, 16% and 6, 32%). Analytical data was identical with that previously described. |