Home Cart 0 Sign in  

[ CAS No. 269410-25-5 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 269410-25-5
Chemical Structure| 269410-25-5
Structure of 269410-25-5 * Storage: {[proInfo.prStorage]}

Quality Control of [ 269410-25-5 ]

Related Doc. of [ 269410-25-5 ]

SDS
Alternatived Products of [ 269410-25-5 ]
Alternatived Products of [ 269410-25-5 ]

Product Details of [ 269410-25-5 ]

CAS No. :269410-25-5 MDL No. :MFCD02093724
Formula : C14H21BO3 Boiling Point : 367.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :248.13 g/mol Pubchem ID :-
Synonyms :

Safety of [ 269410-25-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 269410-25-5 ]

  • Downstream synthetic route of [ 269410-25-5 ]

[ 269410-25-5 ] Synthesis Path-Downstream   1~25

  • 1
  • [ 2374-05-2 ]
  • [ 25015-63-8 ]
  • [ 269410-25-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: With triethylamine In 1,4-dioxane at 80℃; for 18h; Stage #2: 4-bromo-2,6-dimethyl-phenol; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With triethylamine In 1,4-dioxane at 100℃; for 336h; 80 2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol [00428] In a reaction vessel under argon, a mixture of a PdCl2(dppf)CH2Cl2 (1.32 g; 1.62 mmol) and triethylamine (3.2 ml; 23 mmol) in dioxane (40 ml; dried over 4 ? sieves) was sealed and stirred at 80 C. overnight (18 h). After cooling to room temperature, HB(pin) (702 ml in dioxane; 1.38 M; 0.97 mol), triethylamine (135 ml; 0.97 mol) and 4-bromo-2,6-dimethylphenol (65 g; 0.323 mol) were added and the reaction mixture was stirred at 100 C. GC analysis after 14 days showed a peak at 11.6 mins which was identified by 1H NMR as the desired compound.
  • 2
  • [ 269410-25-5 ]
  • [ 864780-59-6 ]
  • [ 864780-61-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In 1,2-dimethoxyethane; water at 95℃; for 5h; 15.d 4-[6-Chloro-1- (2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-6-(4- hydroxy-3,5-dimethylphenyl)-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin- 3-one 6-Chloro-4-[6-chloro-1-(2-trimethylsilanylethoxymethyl)-1 H-benzimidazol-2-yl]-2-(2- trimethylsilanylethoxymethyl)-2H-pyridazin-3-one (100 mg; 0.185 mmol) and tetrakis (triphenylphosphine) palladium (0) (0.15 equivalents) are dissolved in DME, and argon is passed in for 10 min. 2, 6-Dimethyl-4- (4, 4,5, 5-tetramethyl-1, 3,2- dioxaborolan-2-yl) phenol (1 equivalent) and 2M aqueous sodium carbonate solution (2 equivalents) are added and the mixture is heated at 95 C for 5 hours. The volatile constituents are removed in vacuo, the residue is taken up in DMF, and the product the product is purified by column chromatography (RP-HPLC, gradient of 0-100% acetonitrile in water (+ 0. 01% trifluoroacetic acid) ).Yield : 64 mg
With potassium carbonate In 1,2-dimethoxyethane; water at 95℃; for 5h;
  • 3
  • [ 269410-25-5 ]
  • [ 869852-16-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-(6-Chloro-3-methoxy-pyridazin-4-yl)-ethanone In 1,2-dimethoxyethane for 0.0833333h; Stage #2: 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenol With sodium carbonate In 1,2-dimethoxyethane; water at 95℃; for 4h; 6.c (c) 1-[6-(4-Hydroxy-3,5-dimethyl-phenyl)-3-methoxy-pyridazin-4-yl]-ethanone 250 mg of 1-(6-Chloro-3-methoxy-pyridazin-4-yl)-ethanone and 232 mg of tetrakis(triphenylphosphine) palladium (0) are dissolved in 5 ml DME and the solution is stirred for 5 min at RT under argon. 400 mg of 2,6-Dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol and 1.4 ml of a 2M aqueous solution of sodium carbonate are added and the reaction solution is stirred at 95°C for 4 h. The reaction solution is filtered through a silica gel cartridge, eluding with dichloromethane. The solvent is removed under reduced pressure. The product is purified by silica gel chromatography, eluding with a gradient of ethyl acetate in heptane. Yield 334 mg. LC-MS (ES+) 273 (M+H)+.
  • 4
  • [ 269410-25-5 ]
  • [ 869852-31-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-(6-Chloro-3-methoxy-pyridazin-4-yl)-propan-1-one In 1,2-dimethoxyethane at 20℃; for 0.0833333h; Stage #2: 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenol With sodium carbonate In 1,2-dimethoxyethane; water at 95℃; for 4h; 24.c (c) 1-[6-(4-Hydroxy-3,5-dimethyl-phenyl)-3-methoxy-pyridazin-4-yl]-propan-1-one 2 g of 1-(6-Chloro-3-methoxy-pyridazin-4-yl)-propan-1-one and 1.73 g of tetrakis(triphenylphosphine) palladium (0) are dissolved in 10 ml DME and the solution is stirred for 5 min at RT under argon. 3 g of 2,6-Dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol and 10 ml of a 2M aqueous solution of sodium carbonate are added and the reaction solution is stirred at 95°C for 4 h. The reaction solution is poured into ethyl acetate and ished with saturated aqueous sodium bicarbonate. The organic phase is dried (MgSO4), filtered and evaporated under reduced pressure. The product is purified by silica gel chromatography, eluding with a gradient of ethyl acetate in heptane, followed by purification by preparative RP-HPLC eluding with a gradient of 0-100% acetonitrile in water (+0.01 % trifluoroacetic acid). Yield 1.69 g. LC-MS (ES+) 287 (M+H)+.
  • 5
  • [ 269410-25-5 ]
  • [ 870098-72-9 ]
  • [ 870098-73-0 ]
YieldReaction ConditionsOperation in experiment
79% With sodium carbonate In DME (dimethoxyethane); water for 5.08333h; Heating / reflux; 119.b 3.30 g 6-(tert-Butyldimethylsiloxymethyl)-2-(6-chloro-3-methoxy-4-yl-pyridazin-4- yl)-indole-1-carboxylic acid tert-butyl ester, 2.11 g 2,6-dimethyl-4-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, 1.37 g sodium carbonate, and 756 mg tetrakis(triphenylphosphine)palladium(0) are dissolved in a mixture of 53 mL dimethoxyethane and 6.5 mL water. Argon is bubbled through the solution for 5 minutes. The mixture is heated to reflux for 5 hours. After diluting with EtOAc, the organic phase is washed with water and brine, dried with MgS04 and concentrated in vacuo. Purification on silica (Flashmaster, heptane/EtOAc) gives 3.06 g (79%) 6-(tert-butyldimethylsiloxymethyl)-2-[6-(4-hydroxy-3,5-dimethyl-phenyl)-3-methoxy- pyridazin-4-yl]-indole-1-carboxylic acid tert-butyl ester.
  • 6
  • [ 269410-25-5 ]
  • 2-(6-chloro-3-methoxy-pyridazin-4-yl)-6-(4-methyl-piperazin-1-ylmethyl)-indole-1-carboxylic acid tert-butyl ester trifluoroacetate [ No CAS ]
  • 2-[6-(4-hydroxy-3,5-dimethyl-phenyl)-3-methoxy-pyridazin-4-yl]-6-(4-methyl-piperazin-1-ylmethyl)-indole-1-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In DME (dimethoxyethane); water for 5.08333h; Heating / reflux; 143.d 500 mg 2-(6-Chloro-3-methoxy-pyridazin-4-yl)-6-(4-methyl-piperazin-1-ylmethyl)- indole-1-carboxylic acid tert-butyl ester, 233 mg 2,6-dimethyl-4-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl) phenol, 180 mg sodium carbonate, and 98 mg tetrakis(triphenylphosphine)palladium(0) are dissolved in a mixture of 6.7 mL dimethoxyethane and 0.85 mL water. Argon is bubbled through the solution for 5 minutes. The mixture is heated to reflux for 5 hours. After diluting with EtOAc, the organic phase is washed with water and brine, dried with MgS04 and concentrated in vacuo. 475 mg crude product are obtained.
  • 7
  • [ 905590-33-2 ]
  • aqueous potassium carbonate [ No CAS ]
  • [ 269410-25-5 ]
  • [ 247940-06-3 ]
  • 4-(3,4-diethoxyphenyl)-N-[4-(4-hydroxy-3,5-diemthylphenyl)-6-phenylpyridin-2-yl]-4-oxobutanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
tris-(dibenzylideneacetone)dipalladium(0); Example 151 4-(3,4-diethoxyphenyl)-N-[4-(4-hydroxy-3,5-dimethylphenyl)-6-phenylpyridin-2-yl]-4-oxobutanamide Using N-(4-chloro-6-phenylpyridin-2-yl)-4-(3,4-diethoxyphenyl)-4-oxobutanamide obtained in Example 43-(3) (22.6 mg), tris(dibenzylideneacetone)dipalladium (1.1 mg), biphenyl-2-yl(dicyclohexyl)phosphine (1.8 mg), 1N aqueous potassium carbonate solution (0.1 mL) and 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (31.0 mg) as starting materials and in the same manner as in Example 119, 4-(3,4-diethoxyphenyl)-N-[4-(4-hydroxy-3,5-dimethylphenyl)-6-phenylpyridin-2-yl]-4-oxobutanamide (12.3 mg) was obtained. HPLC (220 nm) purity 84% (retention time 1.93 min) MS (ESI+, m/e) 539 (M+H)
  • 8
  • [ 905590-58-1 ]
  • aqueous potassium carbonate [ No CAS ]
  • [ 269410-25-5 ]
  • [ 247940-06-3 ]
  • 4-(2,3-dihydro-1-benzofuran-5-yl)-N-[4-(4-hydroxy-3,5-dimethylphenyl)-6-phenylpyridin-2-yl]-4-oxobutanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
tris-(dibenzylideneacetone)dipalladium(0); Example 183 4-(2,3-dihydro-1-benzofuran-5-yl)-N-[4-(4-hydroxy-3,5-dimethylphenyl)-6-phenylpyridin-2-yl]-4-oxobutanamide Using N-(4-chloro-6-phenylpyridin-2-yl)-4-(2,3-dihydro-1-benzofuran-5-yl)-4-oxobutanamide obtained in Example 114-(1) (20.3 mg), tris(dibenzylideneacetone)dipalladium (1.1 mg), biphenyl-2-yl(dicyclohexyl)phosphine (1.8 mg), 1N aqueous potassium carbonate solution (0.1 mL) and 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (31.0 mg) as starting materials and in the same manner as in Example 119, 4-(2,3-dihydro-1-benzofuran-5-yl)-N-[4-(4-hydroxy-3,5-dimethylphenyl)-6-phenylpyridin-2-yl]-4-oxobutanamide (7.3 mg) was obtained. HPLC (220 nm) purity 94% (retention time 1.86 min) MS (ESI+, m/e) 493 (M+H)
  • 9
  • [ 269410-25-5 ]
  • [ 106-94-5 ]
  • [ 1075196-45-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetone at 65℃; for 96h; 58.1 A mixture 2,6-Dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (500 mg, 2.02 mmol, 1 eq.), 1-bromopropane (793 mg, 6.45 mmol, 3.2 eq.), and K2CO3 (334 mg, 2.42 mmol, 1.2 eq.) in acetone (20 mL) is heated at 65° C. for 4 days. After cooling to room temperature, the reaction is concentrated, diluted with EtOAc and sequentially washed with H2O and saturated aqueous NaCl. The organic solution is dried over Na2SO4 and concentrated to give 2-(3,5-Dimethyl-4-propoxy-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane as a clear oil.
  • 10
  • [ 269410-25-5 ]
  • [ 619-42-1 ]
  • [ 1164100-68-8 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate In water; N,N-dimethyl-formamide at 80℃; for 1h; 109.A Step A: Methyl 4'-hydroxy-3',5'-dimethylbiphenyl-4-carboxylate; A solution of 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (525 mg, 2.12 mmol), methyl 4-bromobenzoate (460 mg, 2.14 mmol), PdCl2(dppf) (80 mg, 0.11 mmol) and Cs2CO3 (1.40 g, 4.31 mmol) in DMF (10 mL, 5% H2O) was heated at 80° C. for 1 h. The reaction mixture was diluted with EtOAc (50 mL), washed with H2O (2×50 mL), and dried over Na2SO4. Purification on a silica gel column gave the desired product as a pale yellow solid (430 mg). NMR (CDCl3): δ 8.08 (d, 2H), 7.62 (d, 2H), 7.29 (s, 2H), 4.75 (s, 1H), 3.95 (s, 3H), 2.35 (s, 6H).
  • 11
  • [ 269410-25-5 ]
  • [ 869852-15-3 ]
  • [ 869852-16-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-(6-Chloro-3-methoxy-pyridazin-4-yl)-ethanone In DME (dimethoxyethane) at 20℃; for 0.0833333h; Stage #2: 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenol With sodium carbonate In DME (dimethoxyethane); water at 95℃; for 4h; 6.c 250 mg of 1-(6-chloro-3-methoxy-pyridazin-4-yl)-ethanone and 232 mg of tetrakis (triphenylphosphine) palladium (0) are dissolved in 5 ml DME and the solution is stirred for 5 min at RT under argon. 400 mg of 2,6-dimethyl-4-(4,4,5,5- tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol and 1.4 ml of a 2M aqueous solution of sodium carbonate are added and the reaction solution is stirred at 95°C for 4 h. The reaction solution is filtered through a silica gel cartridge, eluting with dichloromethane. The solvent is removed under reduced pressure. The product is purified by silica gel chromatography, eluting with a gradient of ethyl acetate in heptane. Yield 334 mg. LC-MS (ES+) 273 (M+H)+.
  • 12
  • [ 269410-25-5 ]
  • [ 869852-30-2 ]
  • [ 869852-31-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-(6-Chloro-3-methoxy-pyridazin-4-yl)-propan-1-one In DME (dimethoxyethane) at 20℃; for 0.0833333h; Stage #2: 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenol With sodium carbonate In DME (dimethoxyethane); water at 95℃; for 4h; 24.c 2 g of 1-(6-chloro-3-methoxy-pyridazin-4-yl)-propan-1-one and 1.73 g of tetrakis (triphenylphosphine) palladium (0) are dissolved in 10 ml DME and the solution is stirred for 5 min at RT (room temperature) under argon. 3 g of 2,6- dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol and 10 ml of a 2M aqueous solution of sodium carbonate are added and the reaction solution is stirred at 95°C for 4 h. The reaction solution is poured into ethyl acetate and ished with saturated aqueous sodium bicarbonate. The organic phase is dried (MgS04), filtered and evaporated under reduced pressure. The product is purified by silica gel chromatography, eluting with a gradient of ethyl acetate in heptane, followed by purification by preparative RP-HPLC eluting with a gradient of 0-100% acetonitrile in water (+0.01 % trifluoroacetic acid). Yield 1.69 g. LC-MS (ES+) 287 (M+H)+.
  • 13
  • [ 269410-25-5 ]
  • [ 1223547-43-0 ]
  • [ 1223547-48-5 ]
  • [ 1223547-45-2 ]
YieldReaction ConditionsOperation in experiment
1: 37% 2: 19% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide; toluene at 80℃;
  • 14
  • [ 269410-25-5 ]
  • [ 1223547-44-1 ]
  • [ 1223547-52-1 ]
  • [ 1223547-49-6 ]
YieldReaction ConditionsOperation in experiment
1: 41% 2: 26% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide; toluene at 80℃;
  • 15
  • [ 2427-70-5 ]
  • [ 269410-25-5 ]
  • [ 1250968-57-0 ]
YieldReaction ConditionsOperation in experiment
33.1% With sodium carbonate In 1,4-dioxane; water at 100℃; for 4h; Inert atmosphere; 2.2.1 Example 2 (reaction according to Scheme 1. step 2); Example 2.1: 4-(3-Aminoquinoxalin-6-yl)-2,6-dimethylphenol; Under argon, 1.66 g (6.7 mmol) of 3,5-dimethyl-4-hydroxyphenylboronic acid pinacol ester, 1.42 g (13.4 mmol) of sodium carbonate dissolved in 10 ml of water and 0.155 g (0.13 mmol) of Pd(PPh3)4 are added to a solution of 0.8 g (4.5 mmol) of 7- chloroquinoxalin-2-ylamine in 40 ml of dioxane, and the mixture is stirred at 1000C for 4 hours.For work-up, 30 ml of ethyl acetate and 30 ml of water are added to the reaction mixture, the phases are separated, the organic phase is dried over magnesium sulphate and filtered and the solvent is removed on a rotary evaporator. The residue obtained is purified by column chromatography on silica gel (ethyl acetate/n-heptane), which gives 0.65 g of 4-(3-aminoquinoxalin-6-yl)-2,6-dimethylphenol.Yield: 33.1 %m.p.: 256°C1H-NMR (600 MHz, DMSO-Qf6) δ= 8.43 (1 H, br. s ), 8.24 (1 H, s), 7.75 (1 H, d), 7.62 (1 H, m), 7.57 (1 H, m), 7.35 (2H, s), 6.90 (2H, s), 2.25 (6H, s) ppmMS (ESI) m/z 266 (MH+)
  • 16
  • [ 269410-25-5 ]
  • [ 1285505-86-3 ]
  • [ 1285505-38-5 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In 1,4-dioxane; water at 90℃; for 2h; 75.1 Example 75Synthesis of N-[(E)-3-(2,4-di(3,5-dimethyl-4-hydroxyphenyl)-phenyl)-2-methyl-acryloyl]-guanidineIntermediate 4 (50 mg, 0.105 mmol) and 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-phenol (62.7 mg, 0.253 mmol) were dissolved in a mixed solution of dioxane and water (v/v=3/1, 2.0 mL). Pd(PPh3)4 (12.2 mg, 0.0105 mmol) and Na2CO3 (133.8 mg, 1.262 mmol) were added to the solution and then stirred at 90° C. for 2 hours. After cooling it to room temperature, the solvent was eliminated in vacuo and then purified by reversed phase HPLC (0.1% TFA in water/CH3CN) to obtain the compound of Example 75 (7.9 mg, 13 W.MS: 444
  • 17
  • [ 269410-25-5 ]
  • [ 947248-68-2 ]
  • [ 1309682-18-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenol With hydrogenchloride In dichloromethane; water for 1.5h; Stage #2: 6-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine With potassium carbonate In propan-1-ol for 2h; Reflux; Int2.1 Intermediate [Example Int2.14-(2-amino[1 , 2, 4]triazolo[1 ,5-a] pyridin-6-yl)-2,6-dimethyl phenol4-Hydroxy-3,5-dimethylphenylboronic acid pinacol ester (700 mg) was dissolved in dichloromethane (2.5 ml) and 2N hydrochloric acid (2.5 ml) was added. It was stirred vigorously for 1 ,5 h and the mixture was extracted with a mixture of dichloromethane an methanol (100: 1 ; 50 ml). The solution was dried (sodium sulfate) and the solvent was removed in vacuum. The residue was dissolved in 1 -propanol (35 ml) and Int1.2 (500 mg), 2M potassium carbonate-solution (3,5 ml), triphenylphosphine (12.6 mg) and PdCl2(PPh3)2 (161 mg) were added. The mixture was heated to reflux for 2h, water (50 ml) was added and the mixture was extracted with ethyl acetate. The solution was dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave 266 mg of the title compound.1 H-NMR (300MHz, DMSO-d6): δ [ppm]= 2.18 (s, 6H), 5.94 (s, 2H), 7.24 (s, 2H), 7.32 (dd, 1 H), 7.64 (dd, 1 H), 8.56 - 8.78 (m, 1 H).
  • 18
  • [ 269410-25-5 ]
  • [ 934826-20-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; water In dichloromethane for 1.5h; 4-Hydroxy-3,5-dimethylphenylboronic acid pinacol ester (700 mg) was dissolved in dichloromethane (2.5 ml) and 2N hydrochloric acid (2.5 ml) was added. It was stirred vigorously for 1,5 h and the mixture was extracted with a mixture of dichloromethane an methanol (100:1; 50 ml). The solution was dried (sodium sulfate) and the solvent was removed in vacuum. The residue was dissolved in 1-propanol (35 ml) and Int1.2 (500 mg), 2M potassium carbonate-solution (3,5 ml), triphenylphosphine (12.6 mg) and PdCl2(PPh3)2 (161 mg) were added. The mixture was heated to reflux for 2h, water (50 ml) was added and the mixture was extracted with ethyl acetate. The solution was dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave 266 mg of the title compound. 1H-NMR (300MHz, DMSO-d6): δ [ppm]= 2.18 (s, 6H), 5.94 (s, 2H), 7.24 (s, 2H), 7.32 (dd, 1 H), 7.64 (dd, 1 H), 8.56 - 8.78 (m, 1 H).
With hydrogenchloride In dichloromethane; water for 0.0833333h; 02.09 To a solution of 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)phenol (777 mg) in dichloromethane was added aqueous hydrochloric acid (c=2N, 7.5 mL). The mixture was vigorously shaken for 5 minutes, the organic phase was separated and the aqueous phase was extracted with a mixture ofdichloromethane and methanol (100:1). The combined organic phases were dried (sodium sulfate) and the solvent was removed in vacuum.The residue (720 mg) was dissolved in 1-propanol (35 mL) and a 2 M potassium carbonate solution (3.5 mL), 6-bromo[1 ,2,4]triazolo[1 ,5-a]pyrazin-2-amine (500 mg), triphenylphosphine (13 mg) and PdCl2(PPh3)2 (164 mg) were added. Themixture was heated to reftux for 3h, water (100 mL) was added and the mixture was extracted with a mixture of ethyl acetate and hexane (3:1). The organic phase was washed with water and with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silicagel chromatography gave a solid that was triturated with ethanol to give 250 mg of the title compound.
  • 19
  • [ 269410-25-5 ]
  • [ 1309680-46-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogenchloride; water / dichloromethane / 1.5 h 2: potassium carbonate; triphenylphosphine / bis-triphenylphosphine-palladium(II) chloride / propan-1-ol / 2 h / Reflux 3: sodium t-butanolate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / tris-(dibenzylideneacetone)dipalladium(0) / 1-methyl-pyrrolidin-2-one / 170 °C / Microwave irradiation
  • 20
  • [ 269410-25-5 ]
  • [ 1309682-18-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogenchloride; water / dichloromethane / 1.5 h 2: potassium carbonate; triphenylphosphine / bis-triphenylphosphine-palladium(II) chloride / propan-1-ol / 2 h / Reflux
  • 21
  • [ 269410-25-5 ]
  • [ 1321517-51-4 ]
  • [ 1321513-22-7 ]
YieldReaction ConditionsOperation in experiment
39% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 150℃; for 2h;
  • 22
  • [ 269410-25-5 ]
  • [ 1404166-45-5 ]
  • [ 1404166-49-9 ]
YieldReaction ConditionsOperation in experiment
60% With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,2-dimethoxyethane; water Inert atmosphere; Reflux;
  • 23
  • [ 269410-25-5 ]
  • 2-bromo-1,3-bis(cyanomethyl)-5-methoxybenzene [ No CAS ]
  • 3',5'-dimethyl-4’-hydroxy-4-methoxybiphenyl-2,6-diacetonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In water; acetonitrile at 120℃; for 0.5h;
  • 24
  • [ 269410-25-5 ]
  • C21H29ClN2O3 [ No CAS ]
  • (S)-methyl 2-(tert-butoxy)-2-[1-(cyclopropylmethyl)-4-(4-hydroxy-3,5-dimethylphenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl]acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl-formamide at 130℃; for 6h; Inert atmosphere; 58.1 Step 1: Preparation of (S)-methyl 2-(tert-butoxy)-2-(1-(cyclopropyl)methyl)-(4-(4-hydroxy-3,5-dimethylphenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate (58a) Step 1: Preparation of (S)-methyl 2-(tert-butoxy)-2-(1-(cyclopropyl)methyl)-(4-(4-hydroxy-3,5-dimethylphenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate (58a) After the compound 1n (260 mg, 0.66 mmol) was dissolved in dimethylformamide (3 mL) under nitrogen, 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenol (188 mg, 1.76 mmol), potassium carbonate (463 mg, 3.35 mmol) and tetrakis(triphenylphosphine)palladium (153 mg, 1.13 mmol) were added thereto, and the mixture was stirred for 6 hours at 130° C. After the reaction material was filtered through a celite pad and washed with ethyl acetate, the filtrate was concentrated under reduced pressure, and then the residue was purified using silica gel column chromatography (ethyl acetate/normal-hexane=1/7) to give a target compound 58a (31 mg, 10%). 1H-NMR (300 MHz, CDCl3) δ 0.41-0.49 (m, 4H), 0.98 (s, 9H), 1.24 (m, 1H), 1.59 (s, 3H), 2.20 (s, 3H), 2.31 (s, 3H), 2.35 (s, 3H), 2.67 (s, 3H), 3.65 (s, 3H), 4.10 (m, 2H), 4.84 (br.s, OH), 5.23 (s, 1H), 6.91 (s, 1H), 7.08 (s, 1H); MS (EI, m/e)=478 (M+).
  • 25
  • [ 269410-25-5 ]
  • 2-[6-(4-hydroxy-3,5-dimethylphenyl)[1,2,4]triazolo[1,5-a]pyrazin-2-yl]amino}benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogenchloride / dichloromethane; water / 0.08 h 2: potassium carbonate; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride / propan-1-ol / 3 h / Reflux 3: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate / toluene; 1-methyl-pyrrolidin-2-one / 5 h / Inert atmosphere; Reflux
Historical Records

Related Functional Groups of
[ 269410-25-5 ]

Organoboron

Chemical Structure| 627906-52-9

[ 627906-52-9 ]

2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Similarity: 1.00

Chemical Structure| 2095797-27-4

[ 2095797-27-4 ]

2-Hydroxy-3-methylphenylboronic acid pinacol ester

Similarity: 0.97

Chemical Structure| 2095797-27-4

[ 2095797-27-4 ]

2-Hydroxy-3-methylphenylboronic acid pinacol ester

Similarity: 0.97

Chemical Structure| 331273-58-6

[ 331273-58-6 ]

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Similarity: 0.97

Chemical Structure| 760989-96-6

[ 760989-96-6 ]

2-(Hydroxymethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Similarity: 0.93

Aryls

Chemical Structure| 627906-52-9

[ 627906-52-9 ]

2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Similarity: 1.00

Chemical Structure| 331273-58-6

[ 331273-58-6 ]

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Similarity: 0.97

Chemical Structure| 760989-96-6

[ 760989-96-6 ]

2-(Hydroxymethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Similarity: 0.93

Chemical Structure| 1487353-52-5

[ 1487353-52-5 ]

2,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Similarity: 0.92

Chemical Structure| 775351-56-9

[ 775351-56-9 ]

2-Hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Similarity: 0.92

Esters

Chemical Structure| 627906-52-9

[ 627906-52-9 ]

2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Similarity: 1.00

Chemical Structure| 2095797-27-4

[ 2095797-27-4 ]

2-Hydroxy-3-methylphenylboronic acid pinacol ester

Similarity: 0.97

Chemical Structure| 331273-58-6

[ 331273-58-6 ]

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Similarity: 0.97

Chemical Structure| 760989-96-6

[ 760989-96-6 ]

2-(Hydroxymethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Similarity: 0.93

Chemical Structure| 2098426-15-2

[ 2098426-15-2 ]

2-Ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Similarity: 0.93