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[ CAS No. 913835-70-8 ]

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Chemical Structure| 913835-70-8
Chemical Structure| 913835-70-8
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Product Details of [ 913835-70-8 ]

CAS No. :913835-70-8 MDL No. :MFCD08436062
Formula : C9H9BN2O3 Boiling Point : 418.2°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :203.99 g/mol Pubchem ID :-
Synonyms :

Safety of [ 913835-70-8 ]

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

Application In Synthesis of [ 913835-70-8 ]

  • Downstream synthetic route of [ 913835-70-8 ]

[ 913835-70-8 ] Synthesis Path-Downstream   1~7

  • 1
  • 6-chloro-4-ethoxy-pyrido[3,2-d]pyrimidin-2-ylamine [ No CAS ]
  • [ 913835-70-8 ]
  • [ 1036386-53-4 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In 1,2-dimethoxyethane; water at 150℃; for 0.166667h; Microwave irradiation; 85 Examples 85 to 87 - synthesis of 6-benzamido-4-ethoxy-pyridor3,2-cflpyrimidin-2-yl- aminesVarious 6-benzamido-4-ethoxy-pyrido[3,2-c/]pyrimidin-2-ylamines were synthesized according to general synthetic sequence outlined in Scheme 17.Scheme 17A mixture of 6-chloro-4-ethoxy-pyrido[3,2-cf]pyrimidin-2-ylamine (15 mg), potassium carbonate (16 mg), tetrakis(triphenylphosphine) palladium (10 mg) and a suitable aryl-boronic acid, or a pinacol ester thereof, (0.08 mmol) in DME (1.5 ml.) and water (0.5 ml_) was heated to 12O0C for 10 minutes by microwave. Solvents were concentrated in vacuuo and the residue was purified by RP HPLC, using a C18 column with a gradient of H2O, 0.1 % TFA-acetonitrile, to provide the desired product. This procedure provided, with yields ranging from 10% to 60% depending upon the aryl group introduced at the 6-position of the pyrido[3,2-c/]pyrimidine ring, the following pure compounds which were characterized by their mass spectrum MS as indicated in the following table 12.
  • 3
  • [ 913835-70-8 ]
  • [ 1453852-15-7 ]
  • [ 1453852-68-0 ]
YieldReaction ConditionsOperation in experiment
61.4% With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In methanol; toluene at 95℃; Inert atmosphere; Sealed tube; 31 Preparation of COMPOUND 104 (2R,3S,4R,5S,6R)-2-(Hydroxymethyl)-6-[2-methyl-3-[4-(5-methyl-l,3,4-oxadiazol-2- yl)phenyl]phenyl]tetrahydropyran-3,4,5-triol In 10 mL microwave vial, to a solution of COMPOUND 76 (31.0 mg, 0.09 mmol) and [4-(5-methyl-l,3,4-oxadiazol-2-yl)phenyl]boronic acid (28.5 mg, 0.14 mmol) in toluene (2.5 mL) and methanol (0.5 mL) is added powdered K3PO4 (39.5 mg, 0.186 mmol) in one portion, degassed (house vacuum/^ flush), Pd(PPh3)4 (16.1 mg, 0.014 mmol) is added in one portion and sealed and heated at 95 °C overnight, filtered through 0.4 micron filter, concentrated and purified by reverse phase HPLC to afford the title compound (24 mg, 61.4%) as white solid XH NMR (400 MHz, CD3OD) δ 8.07 (d, J = 8.3 Hz, 2H), 7.55 (d, J = 7.5 Hz, 1H), 7.48 (d, J = 8.3 Hz, 2H), 7.28 (t, J = 7.7 Hz, 1H), 7.16 (d, J = 6.7 Hz, 1H), 5.20 (d, J = 7.0 Hz, 1H), 4.26 (dd, J = 6.9, 3.3 Hz, 1H), 4.08 - 3.97 (m, 2H), 3.88 - 3.80 (m, 1H), 3.75 (dd, J = 11.9, 3.8 Hz, 1H), 3.68 - 3.58 (m, 1H), 2.63 (s, 3H), 2.32 (s, 3H). LC-MS: m/z = 413.37 (M+H+).
  • 4
  • [ 913835-70-8 ]
  • [ 1453852-17-9 ]
  • [ 1453852-72-6 ]
YieldReaction ConditionsOperation in experiment
34.7% With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐3‐sulfonate; palladium diacetate; potassium carbonate In 2-methyltetrahydrofuran; water at 90℃; for 20h; 31 Preparation of COMPOUND 106 (2R,3S,4R,5S,6R)-2-[2-Fluoro-3-[4-(5-methyl-l,3,4-oxadiazol-2-yl)phenyl]phenyl]-6- (hydroxymethyl)tetrahydropyran-3 ,4,5-triol To a degassed mixture of [3-(2-dicyclohexylphosphanylphenyl)-2,4-dimethoxy- phenyl]sulfonyloxysodium (84.3 mg, 0.1644 mmol), COMPOUND 78 (50 mg, 0.1644 mmol), [3-(2-dicyclohexylphosphanylphenyl)-2,4-dimethoxy-phenyl]sulfonyloxysodium (84.3 mg, 0.164 mmol), [4-(5-methyl-l,3,4-oxadiazol-2-yl)phenyl]boronic acid (50.30 mg, 0.2466 mmol) and K2C03 (114 mg, 0.82 mmol) in 2-Me THF (1.2 mL) and water (240 μ,) is added Palladium (II) acetate (18.5 mg, 0.082 mmol), reaction mixture is slowly heated to 90 °C, stirrer for 20 hours, filtered through celite, washed with 10%H2O-methanol, concentrated, purified on 25 g CI 8 SNAP silica gel cartridge using acetonitrile in water (10% to 40%) as eluent, followed by further purification on reverse phase HPLC to afford the title compound (25 mg, 34.7%) as white solid. XH NMR (400 MHz, CD3OD) δ 8.11 - 8.04 (m, 2H), 7.72 (dd, J = 8.3, 1.3 Hz, 2H), 7.70 - 7.64 (m, 1H), 7.45 (td, J = 7.5, 1.6 Hz, 1H), 7.30 (t, J = 7.7 Hz, 1H), 5.23 (d, J = 7.2 Hz, 1H), 4.19 (dd, J = 7.2, 2.4 Hz, 1H), 4.11 - 4.01 (m, 1H), 3.90 - 3.74 (m, 4H), 2.62 (s, 3H). LC-MS: m/z = 417.19 (M+H+).
  • 5
  • [ 913835-70-8 ]
  • [ 1453855-56-5 ]
  • (2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(4'-(5-methyl-1,3,4-oxadiazol-2-yl)-[1,1'-biphenyl]-3-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,4-dioxane at 90℃; for 4h; Inert atmosphere; 12.IV Step TV7: (2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(4'-(5-methyl-l,3,4-oxadiazol-2-yl)-[l, l'- biphenyl]-3-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate In a 1L 3 necks round bottom flask equipped with a condenser, heating mantle, magnetic stirrer and N 2 inlet is dissolved [(2R,3R,4R,5R,6R)-3,4,5-triacetoxy-6-(3- bromophenyl)tetrahydropyran-2-yl]methyl acetate (18.1 g, 37.14 mmol) , [4-(5 -methyl- 1,3,4- oxadiazol-2-yl)phenyl]boronic acid (12.50 g, 61.28 mmol) and sodium bicarbonate (132.6 mL of 1.4 M, 185.7 mmol) in dioxane (543.0 mL). Pd(PPh3)4 (4.292 g, 3.714 mmol) is then added and the mixture (yellow thick slurry) is stirred at 90°C for 4h. The reaction mixture is cooled to room temperature, filtered over celite to remove inorganic salts and the filtrate is concentrated. The residue is dissolved back in 250mL of EtOAc, adsorb on 50 g of silca gel then purify in two batches on 340g Snap Ultra cartridge with a gradient from 30-80% EtOAc/Hexanes. The appropriated fractions are merged, and then evaporated to afford the title compound (11.74g, 56%) XH NMR (400 MHz, Chloroform-d) δ 8.13 (d, J = 8.4 Hz, 2H), 7.84 - 7.76 (m, 3H), 7.63 (dd, J = 5.8, 2.0 Hz, 1H), 7.54 (dd, J = 4.9, 1.7 Hz, 2H), 6.08 (t, J = 3.1 Hz, 1H), 5.37 (t, J = 9.0 Hz, 1H), 5.20 (dd, J = 9.2, 3.0 Hz, 2H), 4.38 (dd, J = 12.1, 6.6 Hz, 1H), 4.19 - 4.06 (m, 1H), 3.83 (ddd, J = 9.0, 6.6, 2.6 Hz, 1H), 2.64 (s, 3H), 2.19 (s, 3H), 2.09 (s, 3H), 2.08 (s, 3H), 2.04 (s, 1H), 2.02 (s, 3H), 1.59 (s, 2H), 1.26 (t, J = 7.2 Hz, 1H).
  • 6
  • [ 913835-70-8 ]
  • 4-bromo-1-isopropyl-7-methyl-N-((6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl)methyl)-1H-indole-6-carboxamide [ No CAS ]
  • 1-isopropyl-7-methyl-4-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)-N-((6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl)methyl)-1H-indole-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; water at 80 - 85℃; for 16.5h; Inert atmosphere; 54 Example 54: l-Isopropyl-7-methyl-4-(4-(5-methyl-l,3,4-oxadiazol-2-yl)phenyl)-N-((6-methyl-2- oxo-4-propyl-l,2-dihydropyridin-3-yl)methyl)-lH-indole-6-carboxamide To a solution of 4-bromo-l-isopropyl-7-methyl-N-((6-methyl-2-oxo-4-propyl-l,2-dihydro pyridin-3-yl)methyl)-lH-indole-6-carboxamide (Example 30, 300 mg, 0.654 mmol) and (4-(5-methyl-l,3,4-oxadiazol-2-yl)phenyl)boronic acid (187 mg, 0.916 mmol) in 1,4- dioxane (5 mL) was added water (2.500 mL) and bubbled argon gas for 30 minutes. PdCi2(dppf)-CH2Cl2 adduct (53.4 mg, 0.065 mmol) was added and the reaction mass was stirred at 80-85 °C for 16 h. After completion of reaction, the reaction mixture was cooled to RT, filtered through celite, added water, extracted with ethyl acetate, concentrated and purified by column chromatography (silica gel, 5 % MeOH in chloroform) to obtain the title compound. Yield: 231 mg (43 ); JH NMR (CDC13, 300 MHz): δ 11.48 (s, 1H), 8.11 (m, 3H), 7.84 (s, 2H), 7.69 (s, 1H), 7.03 (s, 1H), 6.62 (s, 1H), 5.90 (s, 1H), 5.27 (m, 1H), 4.34 (s, 2H), 2.70 (s, 3H), 2.61 (m, 2H), 2.55 (s, 3H), 2.12 (s, 3H), 1.58 (m, 2H), 1.49 (d, 6H, J=6.9Hz), 0.90 (m, 3H); MS (ESI+): m/z 538 (M+l)+; HPLC purity: 93.47 %.
  • 7
  • [ 913835-70-8 ]
  • 3-chloro-5-oxadiazol-2-yl pyridine [ No CAS ]
  • 3-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)-5-(1,3,4-oxadiazol-2-yl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With [1,1-bis(di-tert-butylphosphino)ferrocene]palladium(II)dichloride; cesium acetate In N,N-dimethyl-formamide at 90℃; for 15h; Sealed tube;
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