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[ CAS No. 937366-54-6 ]

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Chemical Structure| 937366-54-6
Chemical Structure| 937366-54-6
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Product Details of [ 937366-54-6 ]

CAS No. :937366-54-6 MDL No. :MFCD09879158
Formula : C14H18BNO2 Boiling Point : 396.0±15.0°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :243.11 g/mol Pubchem ID :-
Synonyms :

Safety of [ 937366-54-6 ]

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 [ 937366-54-6 ]

  • Downstream synthetic route of [ 937366-54-6 ]

[ 937366-54-6 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 476004-82-7 ]
  • [ 937366-54-6 ]
YieldReaction ConditionsOperation in experiment
With tetrabutyl ammonium fluoride
  • 3
  • [ 937366-54-6 ]
  • C22H22ClN5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Pd(PPh3)4 / 1,2-dimethoxy-ethane 2: 2-methoxy-ethanol
  • 4
  • [ 937366-54-6 ]
  • C25H27ClN6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Pd(PPh3)4 / 1,2-dimethoxy-ethane 2: 2-methoxy-ethanol
  • 5
  • [ 123191-00-4 ]
  • [ 937366-54-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 83 percent / 1/2[IrCl(COD)]2-(4,4'-di-tert-butyl-2,2'-bipyridine) / octane / 16 h / 80 °C 2: TBAF
  • 6
  • [ 73183-34-3 ]
  • [ 937366-54-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 83 percent / 1/2[IrCl(COD)]2-(4,4'-di-tert-butyl-2,2'-bipyridine) / octane / 16 h / 80 °C 2: TBAF
Multi-step reaction with 2 steps 1: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) / hexane / 0.33 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox 2: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane / hexane / 4 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox
Multi-step reaction with 2 steps 1: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) / hexane / 2 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox 2: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane / hexane / 4 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox
  • 7
  • [ 942070-45-3 ]
  • [ 937366-54-6 ]
  • 8
  • 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole [ No CAS ]
  • [ 25015-63-8 ]
  • [ 937366-54-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere; Glovebox 2: methanol / tetrahydrofuran / 20 °C / Inert atmosphere; Glovebox
  • 9
  • [ 120-72-9 ]
  • [ 937366-54-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / benzene-d6 / 0.5 h / 80 °C / Inert atmosphere; Glovebox; Sealed tube 2: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere; Glovebox 3: methanol / tetrahydrofuran / 20 °C / Inert atmosphere; Glovebox
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / dichloromethane / 5 h / 0 - 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: 5 h / 20 °C
Multi-step reaction with 2 steps 1: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) / hexane / 0.33 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox 2: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) / hexane / 4 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox
Multi-step reaction with 2 steps 1: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) / hexane / 0.33 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox 2: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane / hexane / 4 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox
Multi-step reaction with 2 steps 1: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) / hexane / 2 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox 2: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane / hexane / 4 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox

  • 10
  • 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole [ No CAS ]
  • [ 937366-54-6 ]
YieldReaction ConditionsOperation in experiment
139 mg With methanol In tetrahydrofuran at 20℃; Inert atmosphere; Glovebox;
94 %Chromat. With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In hexane at 60℃; for 4h; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;
  • 11
  • 4-(4-chloro-6-methoxy-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole [ No CAS ]
  • [ 76-05-1 ]
  • [ 937366-54-6 ]
  • (x)C2HF3O2*C24H18FN5O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% Stage #1: 4-(4-chloro-6-methoxy-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole; 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 20℃; for 14h; Reflux; Stage #2: trifluoroacetic acid In 1,2-dimethoxyethane; water for 0.25h; 7.A General procedure: Method A: CD54 (33 mg, 0.1 mmol), 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole (66 mg, 0.3 mmol), and K2CO3 (70 mg, 0.5 mmol) were added to a round-bottom flask. DME (6 mL) and water (4 mL) were added at room temperature. The solution was degassed, then Pd(PPh3)4 (10-15 mg, 0.008-0.012 mmol) was added in one portion. The solution was degassed again, then heated at reflux for 14 h. The aqueous layer was extracted with ethyl acetate and 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. 35 TFA salt was isolated as a colorless solid (16 mg, 41%).
  • 12
  • N-[4-(2-bromothiazol-4-yl)-3-chlorophenyl]-1,1,1-trifluoro-methanesulfonamide [ No CAS ]
  • [ 937366-54-6 ]
  • N-{3-chloro-4-[2-(1H-indol-3-yl)-1,3-thiazol-4-yl]phenyl}-1,1,1-trifluoromethanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
42 mg With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 100℃; for 18h; Inert atmosphere; 43 Example 43. Preparation of Compound No. 93 Example 43. Preparation of Compound No. 93 [0201] N-(4-(2-Bromothiazol-4-yl)-3-chlorophenyl)-l,l,l-trifluoromethane sulfonamide (100 mg, 0.2380 mmol) and 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-indole (64 mg, 0.261 mmol), sodium carbonate (63 mg, 0.595), dimethyl formamide (4 mL), water (1.0 mL) were charged in a 25 mL glass bottle and aerated with nitrogen gas for 5 min. After adding Pd(PPh3)4 (27.4 mg, 0.0238 mmol) the mixture was further purged for 2 min and was heated to 100 °C for 18 h. The reaction was monitored by LCMS. The reaction mixture was cooled to RT, water (10 mL) was added and the mixture extracted with EtOAc (3x25 mL). The combined organic layer was washed with water (4x30 mL), dried over sodium sulfate and concentrated under reduced pressure to obtain the crude product, which was purified by reverse phase HPLC to afford N-{3- chloro-4-[2-( 1 H-indol-3-yl)- 1 ,3-thiazol-4-yl]phenyl} -1,1,1 -trifluoromethanesulfonamide (42 mg) as a white solid. 1H NMR (400 MHz, Methanol-d4) δ (ppm): 8.24 - 8.19 (m, 1H), 8.03 (d, J = 8.5 Hz, 1H), 7.98 (s, 1H), 7.77 (s, 1H), 7.50 - 7.45 (m, 2H), 7.36 (dd, J = 8.5, 2.3 Hz, 1H), 7.26 - 7.20 (m, 2H). LCMS (M+l): 458.3.
43 mg With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 100℃; for 18h; Inert atmosphere; 43 Preparation of Compound No. 93 N-(4-(2-Bromothiazol-4-yl)-3-chlorophenyl)-1,1,1-trifluoromethane sulfonamide (100 mg, 0.2380 mmol) and 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (64 mg, 0.261 mmol), sodium carbonate (63 mg, 0.595), dimethyl formamide (4 mL), water (1.0 mL) were charged in a 25 mL glass bottle and aerated with nitrogen gas for 5 min. After adding Pd(PPh3)4 (27.4 mg, 0.0238 mmol) the mixture was further purged for 2 min and was heated to 100° C. for 18 h. The reaction was monitored by LCMS. The reaction mixture was cooled to RT, water (10 mL) was added and the mixture extracted with EtOAc (3*25 mL). The combined organic layer was washed with water (4*30 mL), dried over sodium sulfate and concentrated under reduced pressure to obtain the crude product, which was purified by reverse phase HPLC to afford N-{3-chloro-4-[2-(1H-indol-3-yl)-1,3-thiazol-4-yl]phenyl}-1,1,1-trifluoromethanesulfonamide (42 mg) as a white solid. 1H NMR (400 MHz, Methanol-d4) δ (ppm): 8.24-8.19 (m, 1H), 8.03 (d, J=8.5 Hz, 1H), 7.98 (s, 1H), 7.77 (s, 1H), 7.50-7.45 (m, 2H), 7.36 (dd, J=8.5, 2.3 Hz, 1H), 7.26-7.20 (m, 2H). LCMS (M+1): 458.3.
42 mg With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 100℃; for 18h; Inert atmosphere; 42 Preparation of Compound No. 93 N-(4-(2-Bromothiazol-4-yl)-3-chlorophenyl)-1,1,1-trifluoromethane sulfonamide (100 mg, 0.2380 mmol) and 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (64 mg, 0.261 mmol), sodium carbonate (63 mg, 0.595), dimethyl formamide (4 mL), water (1.0 mL) were charged in a 25 mL glass bottle and aerated with nitrogen gas for 5 min. After adding Pd(PPh3)4 (27.4 mg, 0.0238 mmol) the mixture was further purged for 2 min and was heated to 100° C. for 18 h. The reaction was monitored by LCMS. The reaction mixture was cooled to RT, water (10 mL) was added and the mixture extracted with EtOAc (3*25 mL). The combined organic layer was washed with water (4*30 mL), dried over sodium sulfate and concentrated under reduced pressure to obtain the crude product, which was purified by reverse phase HPLC to afford N-{3-chloro-4-[2-(1H-indol-3-yl)-1,3-thiazol-4-yl]phenyl}-1,1,1-trifluoromethanesulfonamide (42 mg) as a white solid. 1H NMR (400 MHz, Methanol-d4) δ (ppm): 8.24-8.19 (m, 1H), 8.03 (d, J=8.5 Hz, 1H), 7.98 (s, 1H), 7.77 (s, 1H), 7.50-7.45 (m, 2H), 7.36 (dd, J=8.5, 2.3 Hz, 1H), 7.26-7.20 (m, 2H). LCMS (M+1): 458.3.
  • 13
  • [ 669-95-4 ]
  • [ 937366-54-6 ]
  • 3-(1H-indol-3-yl)-4,6-dimethyl-2H-pyran-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 24h;
  • 14
  • [ 670-35-9 ]
  • [ 937366-54-6 ]
  • 3-(1H-indol-2-yl)-4-methoxy-6-methyl-2H-pyran-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 24h;
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