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[ CAS No. 870837-43-7 ] {[proInfo.proName]}

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Chemical Structure| 870837-43-7
Chemical Structure| 870837-43-7
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Product Details of [ 870837-43-7 ]

CAS No. :870837-43-7 MDL No. :
Formula : C12H13NO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 187.24 Pubchem ID :-
Synonyms :

Safety of [ 870837-43-7 ]

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Application In Synthesis of [ 870837-43-7 ]

* 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 [ 870837-43-7 ]

[ 870837-43-7 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 870837-43-7 ]
  • [ 1242336-69-1 ]
  • [ 2763537-59-1 ]
YieldReaction ConditionsOperation in experiment
4% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; triethylamine In N,N-dimethyl-formamide at 140℃; Sealed tube; Inert atmosphere; 27 Example 27: (E)-N-(2,3-dihydro-1H-inden-1-yl)-3-(5-fluoro-1H-benzo[d][1,2,3]triazol-6-yl) acrylamide Into a 8-mL sealed tube purged and maintained with an inert atmosphere of nitrogen, was placed N-(2,3-dihydro-1H-inden-1-yl)prop-2-enamide (Example 24, Step 1, 100.0 mg, 0.53 mmol, 1.0 equiv), 5-bromo-6-fluoro-3H-1,2,3-benzotriazole (138.44 mg, 0.64 mmol, 1.20 equiv), Pd(dppf)Cl2.CH2Cl2 (43.61 mg, 0.05 mmol, 0.10 equiv), DMF (4.0 mL), Et3N (0.22 mL, 1.60 mmol, 3.0 equiv). The resulting solution was stirred overnight at 140 °C. The reaction mixture was cooled to room temperature. The crude mixture was purified by Prep-HPLC. This resulted in 6.3 mg (4%) of (E)-N-(2,3-dihydro-1H-inden-1-yl)-3-(5-fluoro-1H-benzo[d][1,2,3]triazol-6-yl) acrylamide as a off-white solid. LC-MS (ES, m/z): [M+H]+=323 1H NMR (300 MHz, DMSO-d6, ppm): δ 8.63 (d, J = 8.1 Hz, 1H), 8.27 (d, J = 6.6 Hz, 1H), 7.82 (d, J = 10.8 Hz, 1H), 7.68 (d, J = 16.2 Hz, 1H), 7.29-7.18 (m, 4H), 6.88 (d, J = 15.9 Hz, 1H), 5.47- 5.40 (m, 1H), 3.01-2.94 (m, 1H), 2.90-2.79 (m, 1H), 2.49-2.44 (m, 1H), 1.92-1.79 (m, 1H).
4% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; triethylamine In N,N-dimethyl-formamide at 140℃; Sealed tube; Inert atmosphere; 27 Example 27: (E)-N-(2,3-dihydro-1H-inden-1-yl)-3-(5-fluoro-1H-benzo[d][1,2,3]triazol-6-yl) acrylamide Into a 8-mL sealed tube purged and maintained with an inert atmosphere of nitrogen, was placed N-(2,3-dihydro-1H-inden-1-yl)prop-2-enamide (Example 24, Step 1, 100.0 mg, 0.53 mmol, 1.0 equiv), 5-bromo-6-fluoro-3H-1,2,3-benzotriazole (138.44 mg, 0.64 mmol, 1.20 equiv), Pd(dppf)Cl2.CH2Cl2 (43.61 mg, 0.05 mmol, 0.10 equiv), DMF (4.0 mL), Et3N (0.22 mL, 1.60 mmol, 3.0 equiv). The resulting solution was stirred overnight at 140 °C. The reaction mixture was cooled to room temperature. The crude mixture was purified by Prep-HPLC. This resulted in 6.3 mg (4%) of (E)-N-(2,3-dihydro-1H-inden-1-yl)-3-(5-fluoro-1H-benzo[d][1,2,3]triazol-6-yl) acrylamide as a off-white solid. LC-MS (ES, m/z): [M+H]+=323 1H NMR (300 MHz, DMSO-d6, ppm): δ 8.63 (d, J = 8.1 Hz, 1H), 8.27 (d, J = 6.6 Hz, 1H), 7.82 (d, J = 10.8 Hz, 1H), 7.68 (d, J = 16.2 Hz, 1H), 7.29-7.18 (m, 4H), 6.88 (d, J = 15.9 Hz, 1H), 5.47- 5.40 (m, 1H), 3.01-2.94 (m, 1H), 2.90-2.79 (m, 1H), 2.49-2.44 (m, 1H), 1.92-1.79 (m, 1H).
  • 2
  • [ 870837-43-7 ]
  • [ 1214900-63-6 ]
  • [ 2763537-66-0 ]
YieldReaction ConditionsOperation in experiment
12% With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; triethylamine In N,N-dimethyl-formamide at 120℃; for 2h; 34 Example 34: (E)-N-(2,3-dihydro-1H-inden-1-yl)-3-(4-fluoro-3-methyl-1H-indazol-6- yl)acrylamide Into a 8-mL vial, was placed 6-bromo-4-fluoro-3-methyl-1H-indazole (Example 24, Step 1, 100.0 mg, 0.44 mmol, 1.0 equiv), N-(2,3-dihydro-1H-inden-1-yl)prop-2-enamide (81.8 mg, 0.44 mmol, 1.0 equiv), Pd(dppf)Cl2 (31.9 mg, 0.04 mmol, 0.10 equiv), Et3N (0.18 mL, 1.31 mmol, 3.0 equiv), DMF (4.0 mL). The resulting solution was stirred for 2 h at 120 °C in an oil bath. The reaction mixture was cooled. The residue was applied onto a silica gel column with PE/THF (1/1). This resulted in 17 mg (12%) of (E)-N-(2,3-dihydro-1H-inden-1-yl)-3-(4-fluoro-3-methyl- 1H-indazol-6-yl)acrylamide as a solid. LC MS (ES, m/z): [M+H]+=336 1H-NMR (300 MHz, DMSO-d6, ppm) δ 13.09 (s, 1H), 8.47 (d, J = 8.1 Hz, 1H), 7.61 (d, J = 15.6 Hz, 1H), 7.48 (s, 1H), 7.35 -7.15 (m, 4H), 7.01 (d, J = 12.0 Hz, 1H), 6.73 (d, J = 15.6 Hz, 1H), 5.49-5.36 (m, 1H), 3.06 -2.76 (m, 2H), 2.56 (s, 3H), 2.47-2.38 (m, 1H), 1.92-1.76 (m, 1H).
12% With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; triethylamine In N,N-dimethyl-formamide at 120℃; for 2h; 34 Example 34: (E)-N-(2,3-dihydro-1H-inden-1-yl)-3-(4-fluoro-3-methyl-1H-indazol-6- yl)acrylamide Into a 8-mL vial, was placed 6-bromo-4-fluoro-3-methyl-1H-indazole (Example 24, Step 1, 100.0 mg, 0.44 mmol, 1.0 equiv), N-(2,3-dihydro-1H-inden-1-yl)prop-2-enamide (81.8 mg, 0.44 mmol, 1.0 equiv), Pd(dppf)Cl2 (31.9 mg, 0.04 mmol, 0.10 equiv), Et3N (0.18 mL, 1.31 mmol, 3.0 equiv), DMF (4.0 mL). The resulting solution was stirred for 2 h at 120 °C in an oil bath. The reaction mixture was cooled. The residue was applied onto a silica gel column with PE/THF (1/1). This resulted in 17 mg (12%) of (E)-N-(2,3-dihydro-1H-inden-1-yl)-3-(4-fluoro-3-methyl- 1H-indazol-6-yl)acrylamide as a solid. LC MS (ES, m/z): [M+H]+=336 1H-NMR (300 MHz, DMSO-d6, ppm) δ 13.09 (s, 1H), 8.47 (d, J = 8.1 Hz, 1H), 7.61 (d, J = 15.6 Hz, 1H), 7.48 (s, 1H), 7.35 -7.15 (m, 4H), 7.01 (d, J = 12.0 Hz, 1H), 6.73 (d, J = 15.6 Hz, 1H), 5.49-5.36 (m, 1H), 3.06 -2.76 (m, 2H), 2.56 (s, 3H), 2.47-2.38 (m, 1H), 1.92-1.76 (m, 1H).
  • 3
  • [ 870837-43-7 ]
  • [ 1206973-12-7 ]
  • [ 2763389-20-2 ]
YieldReaction ConditionsOperation in experiment
5% With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; triethylamine In N,N-dimethyl-formamide at 120℃; for 15h; 35 Example 35: (E)-N-(2,3-dihydro-1H-inden-1-yl)-3-(1H-pyrazolo[4,3-c]pyridin-6- yl)acrylamide Into a 8-mL vial, was placed 6-bromo-1H-pyrazolo[4,3-c]pyridine (Example 9, Step 1, 200.0 mg, 1.01 mmol, 1.00 equiv), N-(2,3-dihydro-1H-inden-1-yl)prop-2-enamide (189.1 mg, 1.01 mmol, 1.00 equiv), Pd(dppf)Cl2 (73.9 mg, 0.10 mmol, 0.10 equiv) and Et3N (0.42 mL, 3.03 mmol, 3.00 equiv) in DMF (5.00 mL). The resulting solution was stirred for 15 h at 120 °C in an oil bath. The reaction mixture was cooled. The crude mixture was purified by Flash-Prep-HPLC. This resulted in 15 mg (5%) of (E)-N-(2,3-dihydro-1H-inden-1-yl)-3-(1H-pyrazolo[4,3-c]pyridin-6- yl)acrylamide as a white solid. LC MS (ES, m/z): [M+H]+=305 1H NMR (300 MHz, DMSO-d6, ppm): δ 9.05 (s, 1H), 8.58 (d, J = 8.1 Hz, 1H), 8.26 (s, 1H), 7.71 (s, 1H), 7.64 (d, J = 15.0 Hz, 1H), 7.33-7.16 (m, 5H), 5.49-5.40 (m, 1H), 3.02-2.81 (m, 2H), 2.46- 2.40 (m, 1H), 1.90-1.81 (m, 1H).
5% With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; triethylamine In N,N-dimethyl-formamide at 120℃; for 15h; 35 Example 35: (E)-N-(2,3-dihydro-1H-inden-1-yl)-3-(1H-pyrazolo[4,3-c]pyridin-6- yl)acrylamide Into a 8-mL vial, was placed 6-bromo-1H-pyrazolo[4,3-c]pyridine (Example 9, Step 1, 200.0 mg, 1.01 mmol, 1.00 equiv), N-(2,3-dihydro-1H-inden-1-yl)prop-2-enamide (189.1 mg, 1.01 mmol, 1.00 equiv), Pd(dppf)Cl2 (73.9 mg, 0.10 mmol, 0.10 equiv) and Et3N (0.42 mL, 3.03 mmol, 3.00 equiv) in DMF (5.00 mL). The resulting solution was stirred for 15 h at 120 °C in an oil bath. The reaction mixture was cooled. The crude mixture was purified by Flash-Prep-HPLC. This resulted in 15 mg (5%) of (E)-N-(2,3-dihydro-1H-inden-1-yl)-3-(1H-pyrazolo[4,3-c]pyridin-6- yl)acrylamide as a white solid. LC MS (ES, m/z): [M+H]+=305 1H NMR (300 MHz, DMSO-d6, ppm): δ 9.05 (s, 1H), 8.58 (d, J = 8.1 Hz, 1H), 8.26 (s, 1H), 7.71 (s, 1H), 7.64 (d, J = 15.0 Hz, 1H), 7.33-7.16 (m, 5H), 5.49-5.40 (m, 1H), 3.02-2.81 (m, 2H), 2.46- 2.40 (m, 1H), 1.90-1.81 (m, 1H).
5% With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; triethylamine In N,N-dimethyl-formamide at 120℃; for 15h; 35 Example 35: (E)-N-(2,3-dihydro-1H-inden-1-yl)-3-(1H-pyrazolo[4,3-c]pyridin-6- yl)acrylamide Into a 8-mL vial, was placed 6-bromo-1H-pyrazolo[4,3-c]pyridine (Example 9, Step 1, 200.0 mg, 1.01 mmol, 1.00 equiv), N-(2,3-dihydro-1H-inden-1-yl)prop-2-enamide (189.1 mg, 1.01 mmol, 1.00 equiv), Pd(dppf)Cl2 (73.9 mg, 0.10 mmol, 0.10 equiv) and Et3N (0.42 mL, 3.03 mmol, 3.00 equiv) in DMF (5.00 mL). The resulting solution was stirred for 15 h at 120 °C in an oil bath. The reaction mixture was cooled. The crude mixture was purified by Flash-Prep-HPLC. This resulted in 15 mg (5%) of (E)-N-(2,3-dihydro-1H-inden-1-yl)-3-(1H-pyrazolo[4,3-c]pyridin-6- yl)acrylamide as a white solid. LC MS (ES, m/z): [M+H]+=305 1H NMR (300 MHz, DMSO-d6, ppm): δ 9.05 (s, 1H), 8.58 (d, J = 8.1 Hz, 1H), 8.26 (s, 1H), 7.71 (s, 1H), 7.64 (d, J = 15.0 Hz, 1H), 7.33-7.16 (m, 5H), 5.49-5.40 (m, 1H), 3.02-2.81 (m, 2H), 2.46- 2.40 (m, 1H), 1.90-1.81 (m, 1H).
  • 4
  • [ 870837-43-7 ]
  • [ 1286734-85-7 ]
  • [ 2763388-86-7 ]
YieldReaction ConditionsOperation in experiment
54% With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; triethylamine In N,N-dimethyl-formamide at 120℃; for 15h; 10 Example 10: (E)-N-(2,3-dihydro-1H-inden-1-yl)-3-(5-fluoro-1H-indazol-6-yl)acrylamide Into a 8-mL round-bottom flask, was placed 6-bromo-5-fluoro-1H-indazole (100.00 mg, 0.46 mmol, 1.00 equiv), N-(2,3-dihydro-1H-inden-1-yl)prop-2-enamide (Example 9, Step 1, 87.08 mg, 0.46 mmol, 1.00 equiv), Pd(dppf)Cl2 (34.03 mg, 0.046 mmol, 0.1 equiv), Et3N (141.2 mg, 1.39 mmol, 3.00 equiv) and DMF (3.00 mL). The resulting solution was stirred for 15 hr at 120 °C in an oil bath. The mixture was cooled to RT and applied onto a silica gel column with THF/PE (1/1). This resulted in 80 mg (54%) of (2E)-N-(2,3-dihydro-1H-inden-1-yl)-3-(5-fluoro- 1H-indazol-6-yl)prop-2-enamide as a white solid. LC-MS (ES, m/z): [M+H]+=322 1H-NMR (300 MHz, DMSO-d6, ppm): δ 13.32 (s, 1H), 8.61 (d, J = 8.1 Hz, 1H), 8.09 (s, 1H), 7.80 (d, J = 6.0 Hz, 1H), 7.71-7.62 (m, 2H), 7.30-7.21 (m, 4H), 6.86 (d, J = 15.9 Hz, 1H), 5.45-5.42 (m, 1H), 2.98-2.85 (m, 2H), 2.52-2.46 (m, 1H), 1.89-1.82 (m, 1H).
54% With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; triethylamine In N,N-dimethyl-formamide at 120℃; for 15h; 10 Example 10: (E)-N-(2,3-dihydro-1H-inden-1-yl)-3-(5-fluoro-1H-indazol-6-yl)acrylamide Into a 8-mL round-bottom flask, was placed 6-bromo-5-fluoro-1H-indazole (100.00 mg, 0.46 mmol, 1.00 equiv), N-(2,3-dihydro-1H-inden-1-yl)prop-2-enamide (Example 9, Step 1, 87.08 mg, 0.46 mmol, 1.00 equiv), Pd(dppf)Cl2 (34.03 mg, 0.046 mmol, 0.1 equiv), Et3N (141.2 mg, 1.39 mmol, 3.00 equiv) and DMF (3.00 mL). The resulting solution was stirred for 15 hr at 120 °C in an oil bath. The mixture was cooled to RT and applied onto a silica gel column with THF/PE (1/1). This resulted in 80 mg (54%) of (2E)-N-(2,3-dihydro-1H-inden-1-yl)-3-(5-fluoro- 1H-indazol-6-yl)prop-2-enamide as a white solid. LC-MS (ES, m/z): [M+H]+=322 1H-NMR (300 MHz, DMSO-d6, ppm): δ 13.32 (s, 1H), 8.61 (d, J = 8.1 Hz, 1H), 8.09 (s, 1H), 7.80 (d, J = 6.0 Hz, 1H), 7.71-7.62 (m, 2H), 7.30-7.21 (m, 4H), 6.86 (d, J = 15.9 Hz, 1H), 5.45-5.42 (m, 1H), 2.98-2.85 (m, 2H), 2.52-2.46 (m, 1H), 1.89-1.82 (m, 1H).
54% With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; triethylamine In N,N-dimethyl-formamide at 120℃; for 15h; 10 Example 10: (E)-N-(2,3-dihydro-1H-inden-1-yl)-3-(5-fluoro-1H-indazol-6-yl)acrylamide Into a 8-mL round-bottom flask, was placed 6-bromo-5-fluoro-1H-indazole (100.00 mg, 0.46 mmol, 1.00 equiv), N-(2,3-dihydro-1H-inden-1-yl)prop-2-enamide (Example 9, Step 1, 87.08 mg, 0.46 mmol, 1.00 equiv), Pd(dppf)Cl2 (34.03 mg, 0.046 mmol, 0.1 equiv), Et3N (141.2 mg, 1.39 mmol, 3.00 equiv) and DMF (3.00 mL). The resulting solution was stirred for 15 hr at 120 °C in an oil bath. The mixture was cooled to RT and applied onto a silica gel column with THF/PE (1/1). This resulted in 80 mg (54%) of (2E)-N-(2,3-dihydro-1H-inden-1-yl)-3-(5-fluoro- 1H-indazol-6-yl)prop-2-enamide as a white solid. LC-MS (ES, m/z): [M+H]+=322 1H-NMR (300 MHz, DMSO-d6, ppm): δ 13.32 (s, 1H), 8.61 (d, J = 8.1 Hz, 1H), 8.09 (s, 1H), 7.80 (d, J = 6.0 Hz, 1H), 7.71-7.62 (m, 2H), 7.30-7.21 (m, 4H), 6.86 (d, J = 15.9 Hz, 1H), 5.45-5.42 (m, 1H), 2.98-2.85 (m, 2H), 2.52-2.46 (m, 1H), 1.89-1.82 (m, 1H).
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