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[ CAS No. 1627722-97-7 ]

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Chemical Structure| 1627722-97-7
Chemical Structure| 1627722-97-7
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Product Details of [ 1627722-97-7 ]

CAS No. :1627722-97-7 MDL No. :MFCD13182067
Formula : C14H19BN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :258.12 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1627722-97-7 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P272-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335-H317 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1627722-97-7 ]

  • Downstream synthetic route of [ 1627722-97-7 ]

[ 1627722-97-7 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 1627722-97-7 ]
  • [ 4595-60-2 ]
  • [ 1632032-36-0 ]
YieldReaction ConditionsOperation in experiment
97% With potassium phosphate; ((2-dicyclohexylphosphino-2',4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2‘-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate) In tert-butyl methyl ether; water at 100℃; for 0.333333h; Microwave irradiation;
  • 2
  • [ 591-50-4 ]
  • [ 1627722-97-7 ]
  • [ 51093-42-6 ]
YieldReaction ConditionsOperation in experiment
74% With potassium phosphate; ((2-dicyclohexylphosphino-2',4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2‘-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate) In tert-butyl methyl ether; water at 100℃; for 0.333333h; Microwave irradiation;
0.081 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 2h;
  • 3
  • [ 108-86-1 ]
  • [ 1627722-97-7 ]
  • [ 51093-42-6 ]
YieldReaction ConditionsOperation in experiment
86% With potassium phosphate; ((2-dicyclohexylphosphino-2',4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2‘-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate) In tert-butyl methyl ether; water at 55℃; for 0.266667h; Microwave irradiation;
  • 4
  • [ 1627722-97-7 ]
  • [ 90-13-1 ]
  • [ 1632032-33-7 ]
YieldReaction ConditionsOperation in experiment
97% With potassium phosphate; ((2-dicyclohexylphosphino-2',4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2‘-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate) In tert-butyl methyl ether; water at 100℃; for 0.333333h; Microwave irradiation;
  • 5
  • [ 65232-57-7 ]
  • [ 1627722-97-7 ]
  • [ 1632032-34-8 ]
YieldReaction ConditionsOperation in experiment
90% With potassium phosphate; ((2-dicyclohexylphosphino-2',4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2‘-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate) In tert-butyl methyl ether; water at 100℃; for 0.333333h; Microwave irradiation;
  • 6
  • [ 623-12-1 ]
  • [ 1627722-97-7 ]
  • [ 51093-44-8 ]
YieldReaction ConditionsOperation in experiment
76% With potassium phosphate; ((2-dicyclohexylphosphino-2',4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2‘-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate) In tert-butyl methyl ether; water at 100℃; for 0.333333h; Microwave irradiation;
  • 7
  • [ 7051-16-3 ]
  • [ 1627722-97-7 ]
  • [ 1632032-35-9 ]
YieldReaction ConditionsOperation in experiment
91% With potassium phosphate; ((2-dicyclohexylphosphino-2',4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2‘-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate) In tert-butyl methyl ether; water at 100℃; for 0.333333h; Microwave irradiation;
  • 8
  • [ 1627722-97-7 ]
  • [ 106-48-9 ]
  • [ 680612-97-9 ]
YieldReaction ConditionsOperation in experiment
84% With potassium phosphate; ((2-dicyclohexylphosphino-2',4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2‘-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate) In tert-butyl methyl ether; water at 100℃; for 0.333333h; Microwave irradiation;
  • 9
  • [ 109-09-1 ]
  • [ 1627722-97-7 ]
  • [ 1429864-72-1 ]
YieldReaction ConditionsOperation in experiment
87% With potassium phosphate; ((2-dicyclohexylphosphino-2',4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2‘-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate) In tert-butyl methyl ether; water at 100℃; for 0.333333h; Microwave irradiation;
  • 11
  • [ 1627722-97-7 ]
  • [ 108-90-7 ]
  • [ 51093-42-6 ]
YieldReaction ConditionsOperation in experiment
71% With potassium phosphate; ((2-dicyclohexylphosphino-2',4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2‘-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate) In tert-butyl methyl ether; water at 55℃; for 16h;
YieldReaction ConditionsOperation in experiment
95% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine In 1,4-dioxane for 3h; Reflux; 6 General procedure: tert-Butyl 3-iodo-2-methyl-1H-indole-1-carboxylate (1.0 g 4.0 mmol) and bis(pinacolato)diboron were dissolved in dioxane. Et3N was added via a syringe followed by Pd(dppf)Cl2. The reaction mixture was refluxed for 3 h. The volatile components were removed on a rotary evaporator the residue was dissolved in ether. The mixture was filtered and ether solution was collected. The volatile components were removed on a rotary evaporator, and the residue was purified by flash column chromatography. tert-Butyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (>50% yield) was isolated with tert-butyl 2-methyl-1H-indole-1-carboxylate as impurity. Using the BuLi method, the desired product was isolated in 67% yield (>90% purity).
  • 13
  • [ 1627722-97-7 ]
  • 4-(4-chloro-6-methoxy-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole [ No CAS ]
  • C24H20N6O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In methanol; water; toluene for 12h; Inert atmosphere; Reflux; 7 Optimized Suzuki coupling conditions previously reported (Jimenez, J.-M. et. al. 2013, J. Med. Chem. DIO: 10.1021/jm301465a) was followed to synthesize Cpd. No. 65. CD54 (34 mg, 0.1 mmol), 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (CD143, 75 mg, 0.3 mmol), and Na2CO3 (50 mg) were mixed in round-bottom flask. To this flask, MeOH (4 mL), PhMe (4 mL), and water (1 mL) were added and the system was degassed and refilled with pure nitrogen. Pd(PPh3)4 (20 mg) was then added. Again, the system was degassed and refilled with pure nitrogen. The mixture was heated at reflux for 12 h. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine and dried over anhydrous Na2SO4. The volatile components were removed on a rotary evaporator and the residue was purified by reverse phase HPLC. The desired product Cpd. No. 65 was isolated as TFA salt in 23% yield. 1H NMR (DMSO-d6, 300 MHz): 12.36 (s, 1H), 9.31 (s, 1H), 9.05 (s, 1H), 8.82 (d, J=8.18 Hz, 1H), 7.85 (d, J=8.48 Hz, 1H), 7.60-7.50 (m, 1H), 7.39 (s, 1H), 7.40-7.32 (m, 1H), 4.36 (s, 3H), 4.00 (s, 3H), 3.37 (s, NH), 2.32 (s, 3H), 2.13 (s, 3H). ESI-MS Calculated for C24H21N6O2 [M+H]+=425.17. Found: 425.83.
  • 14
  • [ 52088-10-5 ]
  • [ 73183-34-3 ]
  • [ 1627722-97-7 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium acetate In 1,4-dioxane at 90℃; for 10h; Inert atmosphere; 11.a 3-Iodo-1-methyl -1H-indazole (11.6g, 45mmol), bis (pinacolato) borate (22.8g, 89.8mmol), potassium acetate (13.2g, 3eq) was suspended in 150ml of anhydrous 1,4-dioxane, and substituted by nitrogen, was added tetrakis (triphenylphosphine) palladium (5.2g, 10% eq), heated under nitrogen to 90 10H reaction, after completion of the reaction monitored by TLC. Cooled to room temperature, suction filtered, the filter cake was washed several times with ethyl acetate bounce combined organic phase was concentrated under reduced pressure to flash column chromatography to give 1-methyl -1H- indazol-3-yl boronic acid pinacol ester crude product (15g), without further purification in the next step directly.
Historical Records

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Esters

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[ N/A ]

5-Bromo-1-methylindazole-3-boronic acid, pinacol ester

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Indazoles

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