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[ CAS No. 916326-10-8 ]

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Chemical Structure| 916326-10-8
Chemical Structure| 916326-10-8
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Product Details of [ 916326-10-8 ]

CAS No. :916326-10-8 MDL No. :MFCD04117940
Formula : C14H20BNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :277.12 g/mol Pubchem ID :-
Synonyms :

Safety of [ 916326-10-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 916326-10-8 ]

  • Downstream synthetic route of [ 916326-10-8 ]

[ 916326-10-8 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 916326-10-8 ]
  • [ 89937-26-8 ]
  • [ 1020658-45-0 ]
YieldReaction ConditionsOperation in experiment
Into a flame-dried Schlenk flask equipped with a magnetic stirbar and under a N2 atmosphere was added 3-(ethoxycarbonyl)pyridine-5-boronic acid pinacol ester (1 equiv.), l-(6- chloropyridazin-3-yl)piperidin-4-ol (1.1 equiv), Pd2(dba)3 (0.01 equiv.) and tricyclohexylphosphine (0.025 equiv.). The flask was evacuated and back-filled with N2 (repeated 3 times). The solids were suspended in dioxane (0.5 M) and then an aqueous solution of tribasic potassium phosphate (1.7 equiv.) was added. The mixture was heated to 100 C in an oil bath for 3 h. The mixture was cooled, poured into a separatory funnel containing pH 5 buffer and the mixture was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and the solvent was evaporated under reduced pressure. Purification by column chromatography on silica gel (eluting with 5% MeOH in ethyl acetate) gave the indicated product as a beige solid
  • 2
  • [ 688357-19-9 ]
  • [ 916326-10-8 ]
  • C17H15N3O4 [ No CAS ]
  • 3
  • [ 20986-40-7 ]
  • [ 73183-34-3 ]
  • [ 916326-10-8 ]
YieldReaction ConditionsOperation in experiment
62% With potassium acetate;tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In N,N-dimethyl-formamide; at 80 - 85℃;Inert atmosphere; Add tris(dibenzylideneacetone)dipalladium(0) (3.98 g, 4.35 mmol), tricyclohexylphosphine (2.44 g, 8.7 mmol) and potassium acetate (42.65 g, 435 mmol) to a solution of bis(pinacolato) diboron (35.88 g, 141.3 mmol) in dimethylformamide (175 mL). Bubbling N2 into the mixture for 15 minutes, then heat it to 80~85 C. Then add ethyl 5-bromonicotinate (25.0 g, 108.8 mmol) in dimethylformamide (75 mL) slowly to the mixture at 80~85 C., and stir the formed mixture at 80~85 C. for 4-5 hours. Cool the reaction mixture to 15-35 C., and then add methyl tertiary butyl ether (250 mL) and water (250 mL). Filter the mixture with diatomite and separate the organic and aqueous layers. Back extract the aqueous layer with methyl tertiary butyl ether (250 mL). Wash the combined organic layer with brine (150 mL) and water (150 mL). Concentrate the organic under vacuum, re-crystallize the crude product with methyl tertiary butyl ether/heptane (1:6), and then dry it below 55 C. to give the title compound as a grey solid (18.67 g, 62%). 1H NMR (acetone-d6, 400 MHz) delta40-1.43 (m, 15H), 4.44 (q, J=7.1 Hz, 2H), 8.57 (t, J=1.9 Hz, 1H), 9.02 (d, J=1.5 Hz, 1H), 9.225 (d, J=2.3 Hz, 1H)
1.5 g With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; tricyclohexylphosphine tetrafluoroborate; In 1,4-dioxane; at 80 - 100℃; for 16h;Inert atmosphere; To a solution of 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2- yl))-1,3,2-dioxaborolane (1.54 g, 6.09 mmol) and tricyclohexylphosphonium tetrafluoroborate (0.1 12 g, 0.304) in 1,4-dioxane (20 mL) at ambient temperature was added KOAc (1.71 g, 17.4 mmol) and the reaction mixture was purged with nitrogen gas for 10 min. The reaction mixture was heated to 80 C. Pd2(dba)3 (0.199 g, 0.217 mmol) was added to the reaction mixture and the resulting reaction mixture purged with nitrogen for 10 min at 80 C. The reaction mixture was heated to 90 C and a solution of ethyl 5- bromonicotinate (1.00 g, 4.35 mmol) in 1,4-dioxane (5 mL) was added. The resulting mixture was stirred at 100 C for 16 h. The reaction mixture was allowed to cool to ambient temperature, filtered through CELITE and the filtrate was concentrated under reduced pressure to obtain ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate (1.50 g). The residue was taken to the next step without further purification. LCMS (Condition 11): retention time 0.52 min, [M+1] = 196.1. 1H NMR (400 MHz, DMSO-d6) delta 1.16 (s, 12 H), 1.35 (t, J= 7.2 Hz, 3 H), 4.36 (q, J= 7.2 Hz, 2 H), 8.43 (dd, J= 1.6 Hz, J = 2.0 Hz, 1 H), 8.95 (d, J= 1.6 Hz, 1 H), 9.16 (br s, 1 H).
With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; tricyclohexylphosphine tetrafluoroborate; In 1,4-dioxane; at 80 - 100℃; for 16h;Inert atmosphere; To the solution of 4,4,5, 5-tetramethyl-2-(4,4,5, 5-tetramethyl(l, 3,2-dioxaborolan- 2-yl))-l,3,2-dioxaborolane (1.54 g, 6.09 mmol) and tricyclohexylphosphonium tetrafluoroborate (0.1 12 g, 0.304) in 1,4-dioxane (20 mL) at ambient temperature was added potassium acetate (1.71 g, 17.4 mmol) and the reaction mixture was purged with nitrogen gas for 10 min. The reaction mixture was heated to 80 C. Pd2(dba)3 (0.199 g, 0.217 mmol) was added to the reaction mixture and again nitrogen was passed through for the next 10 min at 80 C. The reaction mixture was heated to 90 C and a solution of ethyl 5-bromonicotinate (1.00 g, 4.35 mmol) in 1,4-dioxane (5 mL) was added. The resulting mixture was stirred at 100 C for 16 h. The reaction mixture was allowed to cool to ambient temperature, filtered through CELITE and the filtrate was concentrated under reduced pressure to obtain ethyl 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)nicotinate (1.5 g). The residue was taken to the next step without further purification. LCMS (Condition 5): retention time 0.52 min, [M+l] = 196.1. XH NMR (400 MHz, DMSO-d6) delta 1.16 (s, 12 H), 1.35 (t, J= 7.2 Hz, 3 H), 4.36 (q, J= 7.2 Hz, 2 H), 8.43 (dd, J = 1.6 Hz, J= 2.0 Hz, 1 H), 8.95 (d, J= 1.6 Hz, 1 H), 9.16 (br s, 1 H).
  • 4
  • [ 916326-10-8 ]
  • [ 1386874-06-1 ]
  • 5
  • [ 38267-96-8 ]
  • [ 916326-10-8 ]
  • [ 1431542-39-0 ]
YieldReaction ConditionsOperation in experiment
60% With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; In water; acetonitrile; at 100℃; for 0.2h;Microwave irradiation; Inert atmosphere; To a mixture of <strong>[38267-96-8]6-bromo-4-chloro-quinazoline</strong> (6g, 23.41 mmol), boronic acid 5-(4,4,5,5- tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-nicotinic acid ethyl ester (6.81 g, 24.58 mmol), Pd(PPh3)2CI2 (0.822g, 1.17 mmol) and K3P04 (7.45g, 35.1 mmol) was added 96 mL of acetonitril. The reaction mixture was flushed with argon and 12ml water was added and the vial capped. The reaction mixture was heated to 100C for 12min using a microwave oven and then cooled down to rt. The mixture was quenched with water, extracted with dichloromethane. The organic layer was washed with brine, dried over MgS04, filtered through a Celite pad and evaporated. The obtained residue was triturated in MeOH to afford the title compound as a light orange solid (5.3g, 95%purity, 60% yield). 1H-NMR (400 MHz, DMSO-d6, 298 K): ? ppm 1.38 (t, 3 H) 4.41 (q, 2 H) 8.1 (d, 1 H) 8.25 (d, 2 H) 8.65 (s, 1 H) 9.22 (s, 1 H) 9.32 (s, 1 H) 9.48 (s, 1 H) . MS: 358.1-360.1 [M+1 ]+, Rt(1) = 1 .28 min.
60% With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; In acetonitrile; at 100℃; for 0.2h;Inert atmosphere; Microwave irradiation; 5-(6-Bromo-quinazolin-4-yl)-nicotinic acid ethyl ester To a mixture of <strong>[38267-96-8]6-bromo-4-chloro-quinazoline</strong> (6 g, 23.41 mmol), boronic acid 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-nicotinic acid ethyl ester (6.81 g, 24.58 mmol), Pd(PPh3)2Cl2 (0.822 g, 1.17 mmol) and K3PO4 (7.45 g, 35.1 mmol) was added 96 mL of acetonitril. The reaction mixture was flushed with argon and 12 ml water was added and the vial capped. The reaction mixture was heated to 100 C. for 12 min using a microwave oven and then cooled down to rt. The mixture was quenched with water, extracted with dichloromethane. The organic layer was washed with brine, dried over MgSO4, filtered through a Celite pad and evaporated. The obtained residue was triturated in MeOH to afford the title compound as a light orange solid (5.3 g, 95% purity, 60% yield). 1H-NMR (400 MHz, DMSO-d6, 298 K): delta ppm 1.38 (t, 3H) 4.41 (q, 2H) 8.1 (d, 1H) 8.25 (d, 2H) 8.65 (s, 1H) 9.22 (s, 1H) 9.32 (s, 1H) 9.48 (s, 1H). MS: 358.1-360.1 [M+1]+, Rt(1')=1.28 min.
  • 6
  • [ 916326-10-8 ]
  • [ 123696-02-6 ]
  • ethyl 5-(5-methoxypyridazin-3-yl)nicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In N,N-dimethyl-formamide; at 85.0℃;Inert atmosphere; Sealed tube; <strong>[123696-02-6]3-chloro-5-methoxypyridazine</strong> (149 mg; commercial), 3-(ethoxycarbonyl)pyridine- 5-boronic acid pinacol ester (289 mg; commercial), K2C03 (276 mg) and Pd(PPh3)4 (173 mg) were suspended in DMF (3.4 mL). The sealed tube was evacuated and refilled with N2 three times. The mixture was then stirred overnight at 85C. The reaction mixture was cooled down to rt and diluted with EA and water. The layers were separated and the aq. phase was extracted twice with EA. The combined org. layers were dried over MgS04 and concentrated under reduced pressure. The crude was purified by prep-HPLC (Method 6) to afford the desired product as a white solid (156 mg; 60% yield). MSI (ESI, m/z): 260.2 [M+H+]; tR = 0.72 min.
  • 7
  • [ 916326-10-8 ]
  • 4-(di-tert-butylphosphino)-N,N-dimethylaniline-dichloropalladium [ No CAS ]
  • [ 62150-45-2 ]
  • ethyl 2'-cyano-3,4'-bipyridine-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Step 1. Ethyl 2'-cyano-3,4'-bipyridine-5-carboxylate A degassed mixture of <strong>[62150-45-2]4-bromopyridine-2-carbonitrile</strong> (1.0 g, 5.5 mmol, Synthonix), ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate (1.5 g, 5.4 mmol, Frontier Scientific), CsF (2 g, 20 mmol), and 4-(di-tert-butylphosphino)-N,N-dimethylaniline-dichloropalladium (2:1) (0.38 g, 0.54 mmol, Aldrich) in 1,4-dioxane (10 mL) and water (3 mL) was heated to 120° C. for 2 hours. Upon cooling to room temperature, EtOAc and H2O were added. The biphasic mixture was filtered. The organic layer was washed with H2O, followed by brine, dried over Na2SO4, filtered and concentrated. The product was purified by flash chromatography, eluting with a gradient from 0-100percent EtOAc/hexanes. The eluent was evaporated and the solid was dried at 40° C. overnight. Yield: 0.9 g, 66percent. LCMS (M+H)+: 254.1.
  • 8
  • [ 916326-10-8 ]
  • [ 62150-45-2 ]
  • Methyl 2-[amino(imino)methyl]-3,4-bipyridine-5-carboxylate [ No CAS ]
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