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[ CAS No. 1616930-46-1 ] {[proInfo.proName]}

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Chemical Structure| 1616930-46-1
Chemical Structure| 1616930-46-1
Structure of 1616930-46-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1616930-46-1 ]

CAS No. :1616930-46-1 MDL No. :MFCD18250656
Formula : C13H21BN2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 280.13 Pubchem ID :-
Synonyms :

Safety of [ 1616930-46-1 ]

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:

Application In Synthesis of [ 1616930-46-1 ]

* 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 [ 1616930-46-1 ]

[ 1616930-46-1 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 88529-79-7 ]
  • [ 25015-63-8 ]
  • [ 1616930-46-1 ]
YieldReaction ConditionsOperation in experiment
78% 4,4?-Di-tert-butyl-2,2?-dipyridyl (194 mg) was added to a solution of (1,5-Cyclooctadiene)(methoxy)-iridium(1) dimer (241 mg) and pinacolborane (4.13 g) in pentane (21 mL) and the mixture was stirred for 20 min at ambient temperature. Then a solution of 1-methyl-1H-pyrazole-3-carboxylate (3.05 g) in pentane (14 mL) and THF (7 mL) was added and the solution was stirred at ambient temperature for 3 d. The volatiles were removed under reduced pressure and the residue was purified by chromatography (SiO2, methylene chloride/methanol) to yield the desired product (78% yield).
78% Intermediate 45a 4,4'-Di-fert-butyl-2,2'-dipyridyl ( 94 mg) was added to a solution of (1 ,5-Cyclooctadiene)(methoxy)- iridium(l) dimer (241 mg) and pinacolborane (4.13 g) in pentane (21 mL) and the mixture was stirred for 20 min at ambient temperature. Then a solution of 1 -methyl-1 /-/-pyrazole-3-carboxylate (3.05 g) in pentane (14 mL) and THF (7 mL) was added and the solution was stirred at ambient temperature for 3 d. The volatiles were removed under reduced pressure and the residue was purified by chromatography (Si02, methylene chloride / methanol) to yield the desired product (78% yield).
78% 4,4?-Di-tert-butyl-2,2?-dipyridyl (194 mg) was added to a solution of (1,5-Cycloocta-diene)(methoxy)iridium(I) dimer (241 mg) and pinacolborane (4.13 g) in pentane (21 mL) and the mixture was stirred for 20 min at RT. Then a solution of 1-methyl-1H-pyrazole-3-carboxylate (3.05 g) in pentane (14 mL) and THF (7 mL) was added and the solution was stirred at RT for 3 d. The volatiles were removed under reduced pressure and the residue was purified by chromatography (SiO2, CH2Cl2/CH3OH) to yield the desired product (78%). [0313] 1H-NMR (DMSO-d6): delta=7.00 (s, 1H), 4.25 (q, J=8 Hz, 2H), 4.04 (s, 3H), 1.31 (s, 3H), 1.28 (t, J=8 Hz, 3H) ppm.
78% 4,4?-Di-ted-butyl-2,2?-dipyridyl (194 mg, 722 pmol) was added to a solution of (1 ,5-Cyclooctadiene)-(methoxy)iridium(l) dimer (241 mg, 363 pmol) and pinacolborane (4.13 g, 32.2 mmol) in pentane (21 mL)and the mixture was stirred for 20 mm at rt. Then a solution of i-methyl-1H-pyrazole-3-carboxylate(3.05 g, 19.8 mmol) in pentane (14 mL) and THF (7 mL) was added and the solution was stirred at rt for3 d. The volatiles were removed under reduced pressure and the residue was purified by chromatography(Si02, CH2CI2 /CH3OH) to yield the desired product (78%).1H-NMR (DMSO-d6): oe = 7.00 (5, 1H), 4.25 (q, J= 8Hz, 2H), 4.04 (s, 3H), 1.31 (s, 3H), 1.28 (t, J = 8Hz,3H) ppm.
78% 4,4'-Di-ferf-butyl-2,2'-dipyridyl (194 mg) was added to a solution of (1 ,5-Cyclooctadiene)- (methoxy)iridium(l) dinner (241 mg) and pinacolborane (4.13 g) in pentane (21 mL) and the RM was stirred for 20 min at RT. Then a solution of 1 -methyl-1 H-pyrazole-3-carboxylate (3.05 g) in pentane (14 mL) and THF (7 mL) was added and the solution was stirred at RT for 3 d. The volatiles were removed under reduced pressure and the residue was purified by chromatography (Si02, CH2CI2 / eOH) to yield the desired product (78%). 1H-NMR (DMSO-de): delta = 7.00 (s, H), 4.25 (q, J = 8 Hz, 2H), 4.04 (s, 3H), 1 .31 (s, 3H), 1 .28 (t, J = 8 Hz, 3H) ppm.
78% 4,4?-Di-tert-butyl-2,2?-dipyridyl (194 mg, 722 pmol) was added to a solution of (1,5-Cyclooctadiene)-(methoxy)iridium(l) dimer (241 mg, 363 pmol) and pinacolborane (4.13 g, 32.2 nimol) in pentane (21 mL) and the mixture was stirred for 20 mm at rt. Then, a solution of 1-methyl-1H-pyrazole-3-carboxylate (3.05 g, 19.8 mmol) in pentane (14 mL) and THF (7 mL) was added and the solution was stirred at rt for 3 d. The volatiles were removed under reduced pressure and the residue was purified by CC (SiC2, CH2CI2 /CH3OH) to yield the desired product (78%).1H-NMR(DMSO-d6): oe = 7.00(s, 1H), 4.25 (q, J= 8Hz, 2H), 4.04(s, 3H), 1.31 (s, 3H), 1.28(t, J 8Hz,3H) ppm.

  • 2
  • [ 468075-00-5 ]
  • [ 1616930-46-1 ]
  • [ 1617523-39-3 ]
YieldReaction ConditionsOperation in experiment
72% With bis-triphenylphosphine-palladium(II) chloride; lithium hydroxide; In N,N-dimethyl-formamide; at 90℃; for 0.5h;Inert atmosphere; A degassed solution of intermediate 45a (900 mg), <strong>[468075-00-5]2-bromo-1-chloro-4-(trifluoromethoxy)benzene</strong> (885 mg), lithium hydroxide (83 mg) and bis(tri-tert-butylphosphine)palladium(0) (84 mg) in dry DMF was stirred under an argon atmosphere at 90 C. for 30 min. The volatiles were removed under reduced pressure and the residue was purified by column chromatography (Interchim cartridge 50SiHP/80 g, Cy/EtOAc) to yield the desired compound (72% yield). [0607] LC-MS (Method 1): m/z [M+H]+=349.2 (MW calc.=348.70); Rt=3.9 min
72% With bis(tri-t-butylphosphine)palladium(0); lithium hydroxide; In N,N-dimethyl-formamide; at 90℃; for 0.5h;Inert atmosphere; Intermediate 45b) A degassed solution of intermediate 45a (900 mg), 2-bromo-1 -chloro-4-(trifluoromethoxy)benzene (885 mg), lithium hydroxide (83 mg) and bis(tri-ferf-butylphosphine)palladium(0) (84 mg) in dry DMF was stirred under an argon atmosphere at 90 C for 30 min. The volatiles were removed under reduced pressure and the residue was purified by column chromatography (Interchim cartridge 50SiHP / 80 g, Cy / EtOAc) to yield the desired compound (72% yield). LC-MS {Method 1): m/z [M+H]+ = 349.2 (MW calc. = 348.70); R, = 3.9 min.
  • 3
  • [ 1027818-88-7 ]
  • [ 1616930-46-1 ]
  • C13H11ClF3N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With bis(tri-t-butylphosphine)palladium(0); lithium hydroxide In N,N-dimethyl-formamide at 80℃; for 1h; 42.1 A degassed mixture of 4-chloro-5-iodo-2-(trifluoromethyl)pyridine (249 mg, 813 μmol), BB-4 (225 mg, 813 μmol), LiOH (20 mg, 906 μmol) and bis(tri-tert-butylphosphine)palladium (26 mg, 57 μmol) in DMF (3.3 mL) was heated to 80° C. for 1 h. The volatiles were removed under reduced pressure and the residue was purified by chromatography (Interchim cartridge50SiHP/12 g, Cy/EtOAc) to yield the desired compound (191 mg, 70%). [0661] LC-MS (Method 2): m/z [M+H]+=334.2 (MW calc.=333.69); Rt=0.87 min.
  • 4
  • [ 152626-78-3 ]
  • [ 1616930-46-1 ]
  • C15H16N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,4-dioxane; water; at 80℃; for 14h;Inert atmosphere; Sealed tube; Step 1: A mixture of I -methyl-5-(4,4, 5,5-tetramethyl-[1 , 3,2]dioxaborolan-2-yl)-1 H-pyrazole-3-carboxylic acid ethyl ester (820 mg, 3.08 mmol), <strong>[152626-78-3]5-bromo-6-methoxy-1H-indazole</strong> (500 mg, 2.2 mmol) and K2C03(1.52 g, 11.0 mmol) in a mixture of dioxane (22 mL) and water (4.4 mL) was degassed with Ar for 30 mm. Bis(tri-tert-butylphosphine)palladium (112 mg, 0.22 mmol) was added to the reaction mixture and heated in sealed tube to 80 C for 14 h. The reaction mixture was cooled and concentrated under reduced pressure, diluted with water and extracted with CH2CI2. The combined organic layers were washed with brine, dried and the volatiles were removed under reduced pressure. The residue was purified bychromatography (SiC2, CH2CI2/CH3OH) to yield the desired compound (320 mg, 50%). LC-MS (method 3): mlz [M-?-H] = 287.0 (MW calc. 286.29); R = 2.64 mm.
  • 5
  • [ 61074-71-3 ]
  • [ 1616930-46-1 ]
  • C12H13ClN2O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With bis(triphenylphosphine)palladium(0); lithium hydroxide In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere; 10.1 A solution of BB-9 (150 mg, 710 pmol), BB-2 (239 mg, 850 pmol), LiOH (20 mg, 850 pmol) and Pd(PPh3)2 (36 mg, 70 μιηοΙ) in dry DMF (5 mL) was heated under Ar to 80°C for 2 h. The volatiles were removed under reduced pressure and the residue was purified by chromatography (Si02, Cy/EtOAc) to yield the desired compound (153 mg, 76%). LC-MS (method 1 ): m/z: [M+Hf = 285.2 (MW calc. = 284.76), R, = 3.8 min. 1H-NMR (CDCI3): δ = 6.75 (s, 2H), 4.42 (q, J = 7.2 Hz, 2H), 3.83 (s, 3H), 2.31 (s, 3H), 1.41 (t, J = 7.2 Hz, 3H) ppm.
  • 6
  • [ 61074-71-3 ]
  • [ 1616930-46-1 ]
  • C15H18N2O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis(triphenylphosphine)palladium(0); lithium hydroxide / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere 2: catacxium A; palladium diacetate; caesium carbonate; water / toluene / 20 h / 90 °C / Inert atmosphere
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