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[ CAS No. 1155264-46-2 ]

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Chemical Structure| 1155264-46-2
Chemical Structure| 1155264-46-2
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Product Details of [ 1155264-46-2 ]

CAS No. :1155264-46-2 MDL No. :MFCD18073255
Formula : C14H20BNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :261.13 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1155264-46-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1155264-46-2 ]

  • Downstream synthetic route of [ 1155264-46-2 ]

[ 1155264-46-2 ] Synthesis Path-Downstream   1~16

YieldReaction ConditionsOperation in experiment
308 mg With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 100℃; for 4h; Inert atmosphere; 7.18 Example 7.17 Preparation of 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-benzo[b][1,4]oxazin-3(4H)-one General procedure: 6-bromo-2H-benzo[b][1,4]oxazin-3(4H)-one (275 mg, 1.21 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (466 mg, 1.84 mmol), potassium acetate (184 mg, 1.87 mmol), and Dichloro 1,1-bis(diphenylphosphino)ferrocene palladium(II) dichloromethane (47 mg, 0.06 mmol) were added to a flask and container was evacuated and backfilled with argon. Reagents were taken up in dioxane (9 mL) and system was again purged with argon. Mixture was then heated at 100° C. for 4 hours. After cooling to rt, reaction mixture was filtered over celite, washing with ethyl acetate. Filtrate was concentrated under reduced pressure and resulting reside was purified by silica gel column chromatography (0-40% ethyl acetate/hexanes) to yield 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-benzo[b][1,4]oxazin-3(4H)-one 7.17 (320 mg).
  • 2
  • [ 1154740-68-7 ]
  • [ 1155264-46-2 ]
YieldReaction ConditionsOperation in experiment
With ammonium formate In methanol for 0.5h; Reflux; 3.7 Step 7: Palladium on activated charcoal (10% Pd by weight, 1.08 g) is added to a mixture of aryl chloride 3g (3.0 g, 10 mmol) and ammonium formate (6.4 g, 0.10 mol) in MeOH (75 mL). The mixture is heated at reflux for 30 min, cooled to RT and filtered through Celite. The filter cake is rinsed with MeOH, the filtrate is concentrated to dryness and the residue is partitioned between water (50 mL) and EtOAc (100 mL). The organic layer is washed with brine (20 mL), dried over anhydrous MgSO4 and concentrated to obtain boronic ester 3h.
  • 3
  • [ 1155264-46-2 ]
  • [ 1256254-52-0 ]
  • [ 1256254-54-2 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate In ISOPROPYLAMIDE; water at 130℃; for 16h; Inert atmosphere; Sealed tube; 4.2 Step 2:To a mixture of chloropyridine 4b (250 mg, 0.64 mmol) in DMA (5.6 mL) is added boronate ester 3h (Example 3) (218 mg, 0.83 mmol), Pd([P(t-Bu)3]2 (33 mg, 0.064 mmol), and NaHCO3 (269 mg, 3.2 mmol), followed by water (565 μL). The mixture is degassed by bubbling with argon under sonication for 10 min, the reaction vessel is sealed and the mixture is heated at 130°C for 16 h. The reaction mixture is diluted with EtOAc (30 mL) and washed with brine (2x), water, and brine, dried over MgSO4, filtered and concentrated and the residue is purified by CombiFlash Companion (30% EtOAc/hexanes) to afford 4c
  • 4
  • [ 1155264-46-2 ]
  • [ 1181329-13-4 ]
  • [ 1229207-42-4 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 125℃; for 0.333333h; Inert atmosphere; Microwave irradiation;
  • 5
  • [ 1155264-46-2 ]
  • [ 814-68-6 ]
  • 1-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)prop-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With N-ethyl-N,N-diisopropylamine In dichloromethane at -78 - 20℃; for 0.5h; 2 To a stirred solution of 1 (200 mg, 0.7 mmol) in DCM (5 mL) was added DIPEA (2.1 mmol), and the solution was cooled to -78 °C. Acryloyl chloride (0.7 mmol) was added and the cold bath removed allowing the reaction to warm to room temperature over 30 min. The reaction was diluted with DCM (25 mL), washed with water (25 mL), dried over sodium sulfate, and concentrated to give the crude product which was purified by flash chromatography to give INT-1 as a white solid (100 mg, 45%): MS m/z (M+H): 316.3
  • 6
  • [ 105655-01-4 ]
  • [ 73183-34-3 ]
  • [ 1155264-46-2 ]
YieldReaction ConditionsOperation in experiment
78% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 95 - 100℃; for 2h;Inert atmosphere; 6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H- benzo[6] [l,4]oxazine (3): To a stirred solution of 6-bromo-3,4-dihydro-2H- benzo[£][l,4]oxazine (2.5 g, 11.6 mmol), bis (pinacolato) diborane (3.56 g, 14.0 mmol) in 1, 4- dioxane (20 mL) was added KOAc (3.4 g, 55.0 mmol) and degassed for 20 min with argon. Then Pd(dppf)2Cl2.DCM (476 mg, 0.58 mmol) was added, again degassed for 5 min, and stirred for 2 h at 95-100 C. After completion of the reaction, the solvent was removed under reduced pressure. Water and ethyl acetate were then added to the reaction mixture, which mixture was then filtered through celite. The filtrate was extracted with ethyl acetate. The combined organic phase was washed with water and brine, dried over anhydrous Na2S04, and concentrated under reduced pressure to afford 3 (2.4 gm, 78% yield) as yellow solid. MS m/z (Mu+Eta): 262.2
42% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 100℃; for 18h;Inert atmosphere; A mixture containing 6-bromo-l-oxa-4-aza-3,4-dihydro-2H-naphthalene (3.51 g, 16.4 mmol), anhydrous KOAc (3.62 g, 36.9 mmol), pinacol diborane (10.4 g, 41.0 mmol) in l,4-dioxane was degassed under bubbling N2 for 15 minutes. PdCl2(dppf) dichloromethane aduct (670 mg, 0.82 mmol) was added and the resulting mixture was stirred and heated to l00C for 18 hours, after which time the reaction was deemed complete by LCMS. The reaction was cooled, filtered through a short pad of CELITE and concentrated in vacuo. The crude residue was purified by silica gel chromatography, eluting with 0-15% hexanes/EtOAc gradient. The product was obtained as a colorless oil. Yield = 1.81 g (6.9 mmol, 42%). (0325) LC/MS - HPLC (254 nm) - Rt 2.65 min. MS (ESI) m/z 262.4 [M+ + H+] Purity = 95 % by UV (0326) (254 nm).
17.1 g With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In 1,4-dioxane;Reflux; The last step of the crude dissolved in dioxane (200ml) added KOAc (15g, 0.15mol), Pd (dppf) 2Cl2 (8.2g, 0.01mol) and 4,4,4 ', 4', 5, 5,5 ', 5'-octamethyl-2,2-bi (1,3,2-dioxaborolane) (38g, 0.15mol), the mixture was stirred at reflux overnight. And concentrated to give crude product on silica gel column chromatography (PE: EtOAc = 1: 1) and purified to give an oily compound 7 (17.1g, 70%).
  • 7
  • [ 1155264-46-2 ]
  • 2'-(4-acryloyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5',6',10',11'-tetrahydrospiro[cyclopropane-1,9'-pyrido[3',4':4,5]pyrrolo[2,3-f]isoquinolin]-7'(8'H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -78 - 20 °C 2: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride / propan-1-ol / 0.33 h / 140 °C / Inert atmosphere; Microwave irradiation
  • 8
  • [ 1155264-46-2 ]
  • C30H30N4O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -78 - 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1 h / 100 °C / Microwave irradiation
  • 9
  • [ 1155264-46-2 ]
  • 2-(4-acryloyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-8,9,10,11-tetrahydro-5H-pyrido[3',4':4,5]pyrrolo[2,3-f]isoquinolin-7(6H)-one trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -78 - 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1 h / 100 °C / Microwave irradiation 3: dichloromethane / 0.5 h / 20 °C
  • 10
  • [ 1155264-46-2 ]
  • C27H27N5O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -78 - 20 °C 2: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / ethanol; 1,2-dimethoxyethane / 6 h / 90 °C / Inert atmosphere
  • 11
  • [ 1155264-46-2 ]
  • 2-(2-(4-acryloyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)pyrimidin-4-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -78 - 20 °C 2: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / ethanol; 1,2-dimethoxyethane / 6 h / 90 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C
  • 12
  • [ 1155264-46-2 ]
  • tert-butyl 2-(4-acryloyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-7-oxo-7,9,10,11-tetrahydro-5H-pyrido[3',4':4,5]pyrrolo[3,2-h]quinazoline-8(6H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -78 - 20 °C 2: sodium carbonate; triphenylphosphine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; bis-triphenylphosphine-palladium(II) chloride / propan-1-ol / 0.33 h / 130 °C / Inert atmosphere; Microwave irradiation
  • 13
  • [ 1155264-46-2 ]
  • 2-(4-acryloyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-8,9,10,11-tetrahydro-5H-pyrido[3',4':4,5]pyrrolo[3,2-h]quinazolin-7(6H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -78 - 20 °C 2: sodium carbonate; triphenylphosphine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; bis-triphenylphosphine-palladium(II) chloride / propan-1-ol / 0.33 h / 130 °C / Inert atmosphere; Microwave irradiation 3: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C
  • 14
  • [ 1155264-46-2 ]
  • 7-(2-(4-acryloyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)pyrimidin-4-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -78 - 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane; water / 2 h / 100 °C / Inert atmosphere
  • 15
  • [ 24036-52-0 ]
  • [ 1155264-46-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: borane-THF / tetrahydrofuran / 3 h / 0 °C / Reflux 2: anhydrous potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 2 h / 95 - 100 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: borane-THF / tetrahydrofuran / 0 °C / Reflux 2: anhydrous potassium acetate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / 1,4-dioxane / Reflux
Multi-step reaction with 2 steps 1: borane-THF / tetrahydrofuran / 70 °C / Inert atmosphere; Cooling with ice 2: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / 1,4-dioxane / 100 °C
  • 16
  • [ 40925-68-6 ]
  • [ 1155264-46-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 4 h / Reflux 2: borane-THF / tetrahydrofuran / 3 h / 0 °C / Reflux 3: anhydrous potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 2 h / 95 - 100 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: anhydrous sodium carbonate / tetrahydrofuran / 20 °C / Inert atmosphere; Cooling with ice 2: borane-THF / tetrahydrofuran / 70 °C / Inert atmosphere; Cooling with ice 3: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / 1,4-dioxane / 100 °C
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