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[ CAS No. 1309980-11-7 ]

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Chemical Structure| 1309980-11-7
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CAS No. :1309980-11-7 MDL No. :MFCD12405017
Formula : C15H23BO3 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :262.15 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1309980-11-7 ]

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 [ 1309980-11-7 ]

  • Downstream synthetic route of [ 1309980-11-7 ]

[ 1309980-11-7 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 1309980-11-7 ]
  • [ 1394070-73-5 ]
  • [ 1394073-04-1 ]
YieldReaction ConditionsOperation in experiment
68.8% With sodium carbonate In 1,4-dioxane; water at 120℃; for 1h; microwave irradiation; 83 Example 83 (R)-2-(2-(3-(2-hydroxypropan-2-yl)phenyl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide A mixture of (R)-2-(2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide (PREPARATION x26, 50 mg, 0.131 mmol), 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ol (51.5 mg, 0.196 mmol), tetrakis(triphenylphospine)palladium (0) (15.13 mg, 0.013 mmol) and sodium carbonate (27.8 mg, 0.262 mmol) in 1,4-dioxane (0.5 mL) and H2O (0.25 mL) was heated to 120° C. in a microwave for 1 hour. After cooling to room temperature, the reaction mixture was diluted with EtOAc, washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography (amine-functionalized silica, 0-10% MeOH gradient in CHCl3) to afford the title compound as an off-white solid (43.4 mg, 0.090 mmol, 68.8%). 1H NMR (400 MHz, DMSO-d6) δ 1.06-1.26 (m, 2H), 1.45 (s, 6H), 1.48-1.71 (m, 3H), 2.91-3.05 (m, 3H), 3.11-3.36 (m, 5H), 3.50-3.67 (m, 2H), 3.73-3.93 (m, 4H), 3.96-4.09 (m, 2H), 4.56 (d, J=11.87 Hz, 1H), 5.04 (s, 1 H), 7.31 (t, J=7.71 Hz, 1H), 7.40-7.47 (m, 1H), 7.51 (s, 1H), 7.99-8.12 (m, 2H), 8.34 (s, 1H). ESI-MS m/z [M+H]+ calc'd for C26H35N5O4, 481.27. found 482.4.
  • 2
  • [ 30951-66-7 ]
  • [ 73183-34-3 ]
  • [ 1309980-11-7 ]
YieldReaction ConditionsOperation in experiment
4.3 g With tetrakis(triphenylphosphine) palladium(0); potassium acetate; In N,N-dimethyl-formamide; at 120℃; for 3h; To a solution of 4.9 g of the compound from the preceding step in 100 ml of DMF are added 7.1 g of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-l,3,2-dioxaborolane, 6.7 g of potassium acetate and then 2.6 g of tetrakis(triphenylphosphine)palladium, and the mixture is heated at 120C for 3 hours. The reaction mixture is concentrated under vacuum, the residue is extracted with EtOAc, the organic phase is washed with water, with 10% aHC03 solution and with saturated NaCl solution, and dried over MgSC^, and the solvent is evaporated off under vacuum. The residue is chromatographed on silica gel, eluting with a cyclohexane/EtOAc mixture in a gradient of from (100/0 v/v) to (90/10 v/v). 4.3 g of the expected compound are obtained.
  • 3
  • [ 618-89-3 ]
  • [ 1309980-11-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: magnesium / diethyl ether / Reflux 1.2: 3 h / Reflux 2.1: potassium acetate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 120 °C
  • 4
  • [ 1309980-11-7 ]
  • [ 1283063-82-0 ]
  • [ 1443151-64-1 ]
YieldReaction ConditionsOperation in experiment
0.385 g With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,2-dimethoxyethane; water for 5h; Reflux; 6 EXAMPLE 6: Compound 56 2-[3-(4-[2-(4-Fluorophenyl)ethyl]amino}-6-methoxy-1,3,5-triazin-2-yl)phenyl]propan-2-ol To a solution of 0.4 g of the compound of Preparation 2.1 in 10 ml of a DME/water mixture (80/20 v/v) are added 0.89 g of the compound of Preparation 3.2 and then 0.82 g of CS2CO3 and 0.1 g of tetrakis(triphenylphosphine)palladium, and the mixture is refluxed for 5 hours. The reaction mixture is concentrated under vacuum, the residue is extracted with EtOAc, the organic phase is washed with saturated NaCl solution, and dried over MgS04, and the solvent is evaporated off under vacuum. The residue is chromatographed on silica gel, eluting with a cyclohexane/EtOAc mixture in a gradient of from (100/0 v/v) to (70/30 v/v). The product obtained is taken up in ether, and the precipitate formed is drained by suction, washed with ether and dried. 0.385 g of the expected compound is obtained.
  • 5
  • [ 1309980-11-7 ]
  • 4-(4-chloro-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole [ No CAS ]
  • 2-(3-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)phenyl)propan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
22% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane; water for 16h; Inert atmosphere; Reflux; 10 2-(3-(7-(3,5-Dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)phenyl)propan-2-ol (free amine) 2-(3-(7-(3,5-Dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)phenyl)propan-2-ol (free amine) [0716] S13 (40 mg, 0.1 mmol, 1.0 equiv.) and 3-(2-hydroxy-2-propanyl)phenylboronic acid pinacol ester (90 mg, 0.3 mmol, 3.0 equiv.) were dissolved in 1,2-dimethoxyethane (4 mL). Sodium carbonate (2.0 M in water, 2 mL) was added. The system was degassed to remove oxygen and nitrogen was refilled. Pd(dppf)Cl2-CH2Cl2 (20 mg, 0.024 mmol, 0.24 equiv.) were added and the system was degassed again and refilled with nitrogen. The reaction mixture was heated at reflux for 16 h. The reaction was quenched with water and extracted with ethyl acetate. The organic layers were combined and removed on a rotary evaporator. The residue was purified by reverse phase HPLC. The HPLC eluents containing the title compound was neutralized with ammonia solution and extracted with ethyl acetate to afford the title compound as free amine (10 mg, 22% yield). 1H NMR (MeOD-d4, 300 MHz): 8.12 (s, 1H), 7.90-7.60 (m, 2H), 7.71 (t, J=7.66 Hz, 1H), 7.50 (s, 1H), 7.31 (s, 1H), 3.66 (s, 3H), 2.89 (s, 3H), 2.30 (s, 3H), 2.12 (s, 3H), 1.63 (s, 6H). ESI-MS calculated for C26H27N4O3 [M+H]+=443.21; Observed: 443.72.
  • 6
  • [ 1309980-11-7 ]
  • 5-(2-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-((tetrahydro-2H-pyran-4-yl)oxy)benzonitrile [ No CAS ]
  • C34H31N3O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; 2,2,2-trifluoroethanol at 140℃; for 1h; 68.1 Example 68: Preparation of 5-(2-(3-(2-hydroxypropan-2-yl)phenyl)-1 H-pyrrolo[2,3- b]pyridin-4-yl)-2-((tetrahydro-2H-pyran-4-yl)oxy)benzonitrile: Step 1 : To a solution of 5-(2-iodo-1 -(phenylsulfonyl)-1 H-pyrrolo[2,3-b]pyridin-4- yl)-2-((tetrahydro-2H-pyran-4-yl)oxy)benzonitrile (75 mgs, 0.128 mmol) and (2-(3- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl)propan-2-ol (35 mgs, 0.154 mmol) in DME (2 mL) was added 2.0 M aqueous Na2C03 (0.2 ml_, 0.4 mmol) and Pd(PPh3)4 (7 mgs, 0.006 mmol) and the reaction mixture was heated at 140 °C for 1 hr. The mixture was then cooled to rt and concentrated and used for next step without purification. LCMS-ESI+ (m/z): [M+H]+ calcd for C34H3105SN3: 594.6; found: 594.2
  • 7
  • [ 1309980-11-7 ]
  • N-[(1S)-1-[[2-chloro-5-[3-(1-hydroxy-1-methyl-ethyl)phenyl]phenyl]methyl]-2-[4-(3,5-dimethyl-1H-pyrazol-4-yl)anilino]-2-oxoethyl]-2-methylpyrazole-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; N,N-dimethyl-formamide / 0.5 h / 80 °C / Microwave irradiation; Inert atmosphere 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 - 80 °C
  • 8
  • [ 1309980-11-7 ]
  • N-[(1S)-1-[[5-[3-(1-amino-1-methylethyl)phenyl]-2-chlorophenyl]methyl]-2-[4-(3,5- dimethyl-1H-pyrazol-4-yl)anilino]-2-oxoethyl]-2-methylpyrazole-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; N,N-dimethyl-formamide / 0.5 h / 80 °C / Microwave irradiation; Inert atmosphere 2: trifluoroacetic acid; sodium azide / chloroform / 20 °C 3: hydrogen; platinum on activated charcoal / ethyl acetate
  • 9
  • [ 1309980-11-7 ]
  • N-[(1S)-1-[[5-[3-(1-azido-1-methylethyl)phenyl]-2-chlorophenyl]methyl]-2-[4-(3,5-dimethyl-1H-pyrazol-4-yl)anilino]-2-oxoethyl]-2-methylpyrazole-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; N,N-dimethyl-formamide / 0.5 h / 80 °C / Microwave irradiation; Inert atmosphere 2: trifluoroacetic acid; sodium azide / chloroform / 20 °C
  • 10
  • [ 1309980-11-7 ]
  • N-[(1S)-1-[(5-bromo-2-chloro-phenyl)methyl]-2-[4-[3,5-dimethyl-1-(2- trimethylsilylethoxymethyl)pyrazol-4-yl]anilino]-2-oxoethyl]-2-methylpyrazole-3-carboxamide [ No CAS ]
  • N-[(1S)-1-[[2-chloro-5-[3-(1-hydroxy-1-methylethyl)phenyl]phenyl]methyl]-2-[4-[3,5-dimethyl-1-(2-trimethylsilylethoxymethyl)pyrazol-4-yl]anilino]-2-oxoethyl]-2-methylpyrazole-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 0.5h; Microwave irradiation; Inert atmosphere; 73 N-[(1S)-1-[[2-chloro-5-[3-(1-hydroxy-1-methyl-ethyl)phenyl]phenyl]methyl]-2-[4-[3,5- dimethyl-1-(2-trimethylsilylethoxymethyl)pyrazol-4-yl]anilino]-2-oxo-ethyl]-2-methyl- pyrazole-3-carboxamide 2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propan-2-ol (30.6 mg, 0.117 mmol) was added to a solution of the compound from Preparation 72 (40.0 mg, 0.058 mmol) in DMF (0.4 mL) in a 5 mL MW vial. A solution of K2CO3 (24.2 mg, 0.003 mmol) in H2O (0.08 mL) was added and the reaction mixture was degassed with argon for 10 min. PdCl2(dppf).DCM (2.37 mg, 0.003 mmol) was added and the vial was capped and stirred for 30 min at 80°C. The reaction mixture was passed through a PTFE filter and purified by acidic HPLC directly to afford the title compound as an off-white solid. (33 mg, 76% yield).LCMS (METHOD 3) (ES): m/z 741.6 [M+H]+, RT = 0.95 min.
  • 11
  • [ 1309980-11-7 ]
  • 3-bromo-6-methoxy-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazine [ No CAS ]
  • 2-(3-(6-methoxy-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-3-yl)phenyl)propan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); potassium carbonate In 1,4-dioxane; water at 85℃; for 16h; Inert atmosphere; 9 Example 9 2-(3-(6-Methoxy-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-3-yl)phenyl)propan-2-ol A sample of 3-bromo-6-methoxy-7-(1-methyl-1H-pyrazol-4-yl)imidazo[12-b]pyridazine (7 mg, 0.023 mmol, see Example 2, Step 5) was dissolved in dioxane (0.38 ml) and was treated with K2CO3 (9.4 mg, 0.068 mmol), 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ol (30 mg, 0.11 mmol) and water (0.076 ml). This solution was degassed with bubbling nitrogen for 5 minutes. Palladium XPhos G2 (3.6 mg, 4.5 μmop was added, the vial was capped, and the solution was stirred at 85° C. After 16 hours, LCMS indicated consumption of the starting material. The solution was cooled to room temperature, diluted with MeOH and water, filtered, and purified by HPLC (pH=2 method) to provide 2-(3-(6-methoxy-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-3-yl)phenyl)propan-2-ol (3.5 mg, 9.6 μmol, 42% yield). LCMS calculated for C20H22 N5O2 (M+H)+: m/z=364.2; found: 364.2.
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