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[ CAS No. 904326-87-0 ]

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Chemical Structure| 904326-87-0
Chemical Structure| 904326-87-0
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CAS No. :904326-87-0 MDL No. :MFCD08690229
Formula : C13H19BN2O3 Boiling Point : 444.4°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :262.11 g/mol Pubchem ID :-
Synonyms :

Safety of [ 904326-87-0 ]

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 [ 904326-87-0 ]

  • Downstream synthetic route of [ 904326-87-0 ]

[ 904326-87-0 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 7169-97-3 ]
  • [ 73183-34-3 ]
  • [ 904326-87-0 ]
YieldReaction ConditionsOperation in experiment
89.1% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100℃;Inert atmosphere; Industrial scale; A 1 L four-necked flask equipped with a magnetic stirrer, a thermometer, a reflux condenser and a bubbler was charged56.41 g (0.264 mol) of 2-acetylamino-5-bromopyridine, 66.02 g (0.26 mol) of bis (pinacolato) diboron and 76.44 g450 mL of dioxane was added and stirred, 1.90 g (0.002589 mol) of ferrocenepalladium chloride was added under the protection of nitrogen, and the mixture was heated to 100 C. for 18 to 24 hours,TLC control to the end of the reaction, the temperature was precipitated solids, beating filtration, methanol was added 500mL dissolved, filtered and evaporated to dryness, plus heptane beating, to give the product 60.08g, yield 89.1%.
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 80℃; for 15h; Method 32; iV-|'5-(4,4,5,5-Tetramethyl-l,3,2-dioxaborolan-2-yl')pyridin-2-yl1acetamide; A mixture of JV"-(5-bromopyridin-2-yl)acetamide (Method 31; 0.450 g, 2.09 mmol), bis(pinacolato)diboron (0.585 g, 2.30 mmol), potassium acetate (0.616 g, 6.27 mmol), and Pd(dppf)Cl2 (0.077 g, 0.105 mmol) in DMF (10 ml) was stirred at 80 0C for 15 h. The reaction mixture was filtered over diatomaceous earth, concentrated under reduced pressure and the residue was used without further purification, m/z 263.
A solution of 2-acetylamino-5-bromopyridine (0.25 g, 0.95 mmol), bispinacolatodiboron (0.27 g, 1.04 mmol) and KOAc (0.14 g, 1.42 mmol) in 1 ,4- dioxane (8.0 mL) was degassed by flushing with nitrogen for 15 min. Tricyclohexylphosphine (0.032 g, 0.11 mmol) and tris(dibenzyledineacetone) dipalladium (0) (0.05 g, 0.047 mmol) was then added to the reaction mixture, which was again degassed by nitrogen for 15 min. The resulting reaction mixture was heated to 8O0C for 3 h. After the completion of the reaction (TLC monitoring), the reaction mixture was filtered through celite bed and the filtrate was concentrated to get the crude residue that was carried forward to the next step without further purification. MS: 263.15 (M+H)+.
  • 2
  • [ 827614-64-2 ]
  • [ 108-24-7 ]
  • [ 904326-87-0 ]
YieldReaction ConditionsOperation in experiment
63.1% With dmap; triethylamine; In dichloromethane; at 20℃; 1. Preparation of N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide To a solution of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (300mg, 1.36mmol) in dichlormethane(15mL) were successively added dimethylaminopyridine(17mg, 0.139mmol), triethylamine(0.21mL, 1.50mmol) and acetic anhydride(153mg, 1.50mmol). The resulting mixture was reacted under stirring at room temperature for several hours. Then the reaction mixture was diluted with dichlormethane, and washed with aqueous saturated ammonium chloride solution. The organic phase was dried with anhydrous magnesium sulfate, filtered, concentrated to produce 225 mg of the target compound in a yield of 63.1%.
52% With dmap; triethylamine; In dichloromethane; at 20℃; for 3.5h; EXAMPLE 9; Procedures for the Synthesis ofN-(5-(7-Chloro-3-(2-chlorobenzyl)-2-oxo-2,3-dihydro-lH- benzo[e][l,4]diazepin-5-yl)pyridin-2-yl)acetamide; Beginning with Tetramethyl-1,3,2- dioxaborolan-2-yl)pyridin-2-amine.; Step l; N-(5-(4,4,5,5-Tetramethyl-l,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide. 5 (4,4,5,5-Tetramethyl-l,3,2-dioxaborolan-2-yl)pyridin-2-amine (0.3 g, 1.36 mmol) was dissolved in dichloromethane (5 niL) and 4-dimethylaminopyridine 17 mg, 0.136 mmol) was added, followed by triethylamine (0.38 mL, 2.73 mmol) then acetic anhydride (0.153, 1.5 mmol). The mixture was stirred at room temperature for 3.5 h then diluted with dichloromethane and washed with NH4Cl (sat aq) then brine. The organic layer was dried (MgSO4), filtered and concentrated. Chromatography eluting with ethyl acetate gave the desired product (187 mg, 52% yield). 1H-NMR (300 MHz, CDCl3) delta 9.3 (s, IH), 8.6 (s, IH), 8.2 (d, IH), 8.05 (d, IH), 2.2 (s, 3H), 1.2 (s, 12H).
With triethylamine; In dichloromethane; at 20℃; To 2-amino-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (120 mg) in dry DCM (3ml) and triethylamine (1.5equiv., 114uL) was added acetic anhydride(l.lequiv., 57ul) and the reaction mixture was stirred at room temperature overnight.Dichloromethane/brine extraction and purification on silica gave 66mg of N-[5-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine-2-yl]-acetamide.[00584] 2-Chloro-6-(4-methanesulfonyl-piperazin- 1 -ylmethyl)-4-morpholin-4-yl- thieno[3,2-d]pyrimidine, prepared via General Procedure B-3, was reacted with N-[5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine-2-yl]-acetamide via General ProcedureA. Purification on silica and ether trituration gave 233. NMR (CDC13): 2.25 (3H, s), 2.67-2.71 (4H, m), 2.81 (3H, s), 3.29-3.33 (4H, m), 3.89 (2H, s), 3.89-3.93 (4H, m), 4.08-4.12 (4H, m), 7.35 (IH, s), 7.97 (IH, br. s), 8.28 (IH, d), 8.71 (IH, d), 9.30 (IH, s). MS (ESI+): MH+532.28 (100%)
225mg With dmap; triethylamine; In dichloromethane; at 20℃; for 0.5h; 4-dimethylaminopyridine (17mg, 0.139mmol), triethylamine (0.19 mL, 1.36mmol) and acetic anhydride (153mg, 1.50mmol) were added sequentially to a solution of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (300mg, 1.36mmol) in dichloromethane (15mL). The reaction mixture was stirred at room temperature for 0.5 h, then diluted with 30mL of dichloromethane, washed with 50mL of a saturated aqueous solution of ammonium chloride. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated to give 225mg of the product.
225 mg With dmap; triethylamine; In dichloromethane; at 20℃; for 0.5h; 4-dimethylaminopyridine (17 mg, 0.139 mmol), triethylamine (0.19 mL, 1.36 mmol) and acetic anhydride (153 mg, 1.50 mmol) were added sequentially to a solution of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (300 mg, 1.36 mmol) in dichloromethane (15 mL). The reaction mixture was stirred at room temperature for 0.5 h, then diluted with 30 mL of dichloromethane, washed with 50 mL of a saturated aqueous solution of ammonium chloride. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated to give 225 mg of the product.

  • 3
  • [ 904326-87-0 ]
  • [ 1160789-85-4 ]
  • [ 1160790-20-4 ]
YieldReaction ConditionsOperation in experiment
48% Stage #1: N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide; 1-(5-bromobenzo[d]thiazol-2-yl)-3-ethylurea With potassium phosphate In water; N,N-dimethyl-formamide for 0.25h; Stage #2: In water; N,N-dimethyl-formamide at 85℃; for 2.25h; 26 A solution of N-(5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide H-B (0.13 g, 0.49 mmol), 1-(5-bromobenzo[d]thiazol-2-yl)-3-ethylurea (0.10 g, 0.33 mmol) and K3PO4 (0.084 g, 0.39 mmol) in DMF-H2O (7.0 mL, 5:2) was degassed by flushing with nitrogen for 15 min. Dichlorobis(triphenylphosphine)-palladium(ll) (0.023 g, 0.033 mmol) was then added to the reaction mixture followed by degassing with nitrogen for another 15 min. The resulting reaction mixture was then heated to 850C for 2 h. After the completion of the reaction (TLC monitoring), the reaction mixture was cooled to room temperature and poured onto ice-cold water followed by extraction with EtOAc (2 x 50 mL). The combined organics was washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude was then purified over silica gel (60-120 M, 2.50% MeOH-DCM) to obtain the desired product (0.057 g, 48%). 1H-NMR (400 MHz, DMSO-d6): δ 1.09 (t, J= 7.20 Hz, 3H), 2.11 (S, 3H), 3.21 (m, 2H), 6.73 (br s, 1 H), 7.55 (d, J= 9.20 Hz, 1 H), 7.92-7.97 (m, 2H)1 8.15 (m, 2H), 8.68 (s, 1 H), 10.58 (br s, 1H) and 10.74 (br s, 1H). MS: 354.09 (M+H) Qualitative HPLC Purity (Acquity BEH C-18, 100 x 2.1 mm, 264 nm): 93.67% (Rt = 4.83 min).
  • 4
  • [ 904326-87-0 ]
  • [ 1160789-85-4 ]
  • [ 1160790-42-0 ]
YieldReaction ConditionsOperation in experiment
39% Stage #1: N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide; 1-(5-bromobenzo[d]thiazol-2-yl)-3-ethylurea With potassium phosphate In water; N,N-dimethyl-formamide for 0.25h; Stage #2: In water; N,N-dimethyl-formamide at 110℃; for 2.25h; 38 A solution of 1-(5-bromo-6-fluoro-benzothiazol-2-yl)-3-ethyl-urea V (0.10 g, 0.31 mmol), N-(5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide (0.17 g, 0.62 mmol) and K3PO4 (0.067 g, 0.31 mmol) in DMF-H2O (2.5 ml_, 2:0.5) was degassed by flushing with nitrogen for 15 min. Dichlorobis(triphenylphosphine)- palladium(ll) (0.022 g, 0.031 mmol) was then added to the reaction mixture followed by degassing with nitrogen for another 15 min. The resulting reaction mixture was then heated to 11O0C for 2 h. After the completion of the reaction (TLC monitoring), the reaction mixture was cooled to room temperature and poured onto ice-cold water followed by extraction with EtOAc (3 x 25 mL). The combined organics was washed with brine, dried (Na2SO^, filtered and concentrated under reduced pressure. The crude was then purified over silica gel (100-200 M, 1.5% MeOH-DCM) and then through prep-HPLC to obtain the desired product (0.046 g, 39%). 1H-NMR (400 MHz, DMSO-d6): δ 1.08 (t, J= 7.20 Hz, 3H), 2.12 (s, 3H), 3.20 (quintet, J= 6.40 Hz, 2H), 6.77 (br s, 1 H), 7.75 (d, J= 6.80 Hz, 1 H)1 7.93 (d, J= 10.40 Hz, 1 H)1 8.01 (d, J= 8.40 Hz, 1H), 8.18 (d, J= 8.80 Hz, 1 H), 8.52 (s, 1H)1 10.63 (br s, 1H) and 10.85 (br s, 1H). MS: 374.20 (M+H)+. Qualitative HPLC Purity (Acquity BEH C-18, 100 x 2.1 mm, 261 nm): 98.72% (Rt = 5.03 min).
  • 5
  • [ 904326-87-0 ]
  • [ 1233524-18-9 ]
  • [ 1233524-20-3 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate In 1,4-dioxane; water at 120℃; for 2h; 3 Example 3 N-(5-{2-[2-Amino-6-(4-methylpiperazin-l-yl)pyriiiιidin-4-yl]-l^^,4-tetrahydroisoquinolin-7- yl}pyridin-2-yl)acetamide; A mixture of 4-(7-bromo-3,4-dihydroisoquinolin-2( 1 H)-y I)-6-(4-methy Ipiperazin- 1 -yl)pyrimidin- 2-amine (15 mg, 0.037 mmol, Example 1), N-[5-(4,4,5,5-tetrarnethyl-l,3,2-dioxaborolan-2-yl)pyridiϖ-2- yl]acetamide (15 mg, 0.056 mmol, Aldrich, Cat. No. 683892), tetrakis(triphenylphosphine)palladium(0) (2.6 mg, 0.0022 mmol, Aldrich, Cat. No. 216666), and potassium phosphate (24 mg, 0.1 1 mmol) in 1,4- dioxane (1 mL) and water (0.2 mL) was heated at 120 0C for 2 hours. The reaction mixture was cooled to r.t. and then concentrated. The residue was dissolved in MeOH and purified by RP-HPLC (pH=10) to afford the desired compound. LCMS (M+H)+: m/z = 459.4.
  • 6
  • [ 904326-87-0 ]
  • [ 1059065-41-6 ]
  • [ 1251949-00-4 ]
YieldReaction ConditionsOperation in experiment
83% With cesium hydroxide; lithium chloride In 1,4-dioxane; water at 100℃; for 3h; Inert atmosphere; 9.2 Step 2; N-(5-(7-Chloro-3-(2-chlorobenzyl)-l-(4-methoxybenzyl)-2-oxo-2,3-dihydro-lH- benzo[e][l,4]diazepin-5-yl)pyridin-2-yl)acetamide. 5,7-Dichloro-3-(2-chlorobenzyl)-l-(4- methoxybenzyl)-lH-benzo[e][l,4]diazepin-2(3H)-one (208 mg, 0.439 mmol), LiCl (56 mg, 1.32 mmol), and CsOH (221 mg, 1.32 mmol) were combined, then a solution of N-(5- (4,4,5, 5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide (115 mg, 0.439 mmol) in 1,4-dioxane (3 mL) was added followed by water (300 uL). The mixture was purged with nitrogen, then tetrakis(triphenylphosphinepalladium(0) (51 mg, 0.044 mmol) was added and the flask was lowered into a 100 0C oil bath and heated at 100 0C for 3 h. The mixture was allowed to cool, then diluted with ethyl acetate and rinsed with water 2x then brine and dried (MgSO4). Chromatography eluting with 40-50% ethyl acetate in hexanes to give a colorless oil (210 mg, 83% yield). MS (ES+) m/z 573.1 (M + 1).
YieldReaction ConditionsOperation in experiment
57%
57% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 85℃; Inert atmosphere; 63.63b Step 34b: N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide (Compound 0602-107) General procedure: Step 34b: N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide (Compound 0602-107)[0334]To a solution of compound 0601-107 (2.5 g, 11.6 mmol) and bis(pinacolato)diboron (4.4 g, 17.5 mmol) in dioxane (100 mL) was added potassium acetate (3.4 g, 35 mmol) and PdCl2(dppf)2 (0.95 g, 1.1 mmol). The mixture was degassed with nitrogen and heated at 85° C. for overnight. The reaction mixture was concentrated under reduced pressure to afford the crude product, which purified by column chromatography (ethyl acetate in petroleum ether, 15% v/v) to give the compound 0602-107 (1.55 g, 51%) as a pink solid. LCMS: 262 [M+1]+. 1H NMR (400 MHz, DMSO-d6) δ 1.29 (s, 12H), 2.03 (s, 3H), 7.30 (s, 1H), 7.31 (d, J=2.0 Hz 1H), 7.73 (d, J=2.0 Hz, 1H), 7.89 (d, J=1.6 Hz, 1H), 9.93 (s, 1H).
57% With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate In 1,4-dioxane at 85℃; Inert atmosphere; 63b N-(3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) acetamide (Compound 0602-107) General procedure: Compound in dioxane (100mL) 0601-107 (2.5g, 11.6mmol) and a solution of bis (pinacolato) diboron (4.4 g, 17.5 mmol), potassium acetate (3.4 g, 35 mmol) and and PdCl2 (dppf) 2 ( 0.95g, 1.1mmol) was added. The mixture was degassed with nitrogen and heated overnight at 85 ° C.. The reaction mixture was concentrated under reduced pressure to give the crude product, which was purified by column chromatography (petroleum ether in ethyl acetate, 15% v / v) to give the compound 0602-107 as a pink solid obtained (1.55 g, 51%).
  • 8
  • [ 904326-87-0 ]
  • [ 1346702-51-9 ]
  • [ 1346704-16-2 ]
YieldReaction ConditionsOperation in experiment
72% With sodium hydrogencarbonate In 1,2-dimethoxyethane; water at 120℃; for 0.333333h; Inert atmosphere; Sealed tube; Microwave irradiation; 108 Example 1086-[6-(Acetylamino)-3-pyridinyl]-W-[(4,6-dimethyl-2-oxo- l,2-dihydro-3-pyridinyl)methyl]- 1 -(1 - m deIn a 25 mL sealable tube under nitrogen were combined 6-bromo-N-[(4,6-dimethyl-2-oxo- l,2-dihydro-3-pyridinyl)methyl]-l-(l-methylethyl)-lH-indazole-4-carboxamide (110 mg, 0.24 mmol), N-[5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-2-pyridinyl]acetamide (104 mg, 0.4 mmol) in DME/water (3 mL: lmL). PdCl2(dppf)-CH2Cl2 (10.76 mg, 0.013 mmol) was added and the resulting mixture was degassed with nitrogen for 10 min. Sodium bicarbonate (66.4 mg, 0.79 mmol) was added, the vessel was sealed, and the insoluble mixture was heated in a microwave at 120 °C for 20 min. Water was added and the solids that precipitated were filtered off. DCM was added to the solids and it was purified by Si02 chromatography (eluent: gradient 100% DCM to 80:20:2DCM/MeOH/NH4OH). Fractions were evaporated. EtOAc was added, it was sonicated and the solids that precipitated were filtered, washed with hexanes and dried to afford the title compound (91 mg, 72%) as a light beige solid. *H NMR (400 MHz, DMSO-c¾) δ ppm 1 1.54 (s, 1 H) 10.65 (s, 1 H) 8.84 (d, J=2.27 Hz, 1 H) 8.64 (t, J=4.93 Hz, 1 H) 8.39 (s, 1 H) 8.25 - 8.30 (m, 1 H) 8.15 - 8.24 (m, 2 H) 7.89 - 7.93 (m, 1 H) 5.89 (s, 1 H) 5.18 (quin, J=6.63 Hz, 1 H) 4.40 (d, J=4.80 Hz, 2 H) 2.22 (s, 3 H) 2.13 (s, 3 H) 2.12 (s, 3 H) 1.51 (s, 3 H) 1.50 (s, 3 H). MS(ES) [M+H]+ 473.1.
  • 9
  • [ 904326-87-0 ]
  • [ 1332450-86-8 ]
  • [ 1332448-72-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 2h; Inert atmosphere; 71 Example No. 71; Preparation of Compound No. 71[0368] To a de-aerated solution of 5-(2-bromophenyl)-2,8-dimethyl-2,3,4,5-tetrahydro-lH- pyrido[4,3-b]indole (100 mg, 0.28 mmol), N-methyl-5-(4,4,5,5-tetramethyl- 1,3,2- dioxaborolan-2-yl)picolinamide (148 mg, 0.56 mmol) and K2C03 (115 mg, 0.84 mmol) in DME-water (2: 1) was added Pd(PPh3)4 (16 mg, 0.014 mmol). The reaction mixture was stirred at 90 °C for 2h, additional Pd (PPh3)4 (16 mg, 0.014 mmol) was added into the reaction mixture and stirring continued at 90 °C for 12h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in EtOAc(30 mL) and washed with water (20 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude material, which was purified by reverse phase HPLC to yield 5-(2-(2,8-dimethyl-3,4-dihydro-lH-pyrido[4,3-b]indol-5(2H)- yl)phenyl)-N-methylpicolinamide as an off-white solid. 1H NMR (TFA salt, CD3OD) d (ppm): 8.21 (d, IH), 7.82 (d, IH), 7.76 (m, 3H), 7.6 (d, 2H), 7.23 (s, IH), 6.9 (d, 2H), 4.7 (m, IH), 4.3 (m, IH), 3.63 (m, IH), 3.42 (m, IH), 2.8-3.1 (m, 7H), 2.6 (m, IH), 2.4 (s, 3H).
  • 10
  • [ 904326-87-0 ]
  • [ 1332450-86-8 ]
  • [ 1332448-95-9 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 0.75h; Inert atmosphere; 83 Example No. 83; Preparation of Compound No. 83[0380] To a de-aerated solution of 5-(2-bromophenyl)-2,8-dimethyl-2,3,4,5-tetrahydro-lH- pyrido[4,3-b]indole (100 mg, 0.281 mmol), 2-acetamidopyridine-5-boronic acid pinacol ester (147 mg, 0.562 mmol) and K2C03 (116 mg, 0.845 mmol) in DME (4 mL)-water (2 mL) was added Pd(PPh3)4 (16 mg, 0.013 mmol). The reaction mixture was stirred at 90 °C for 45 min. The reaction mixture was concentrated under reduced pressure to dryness. The residue was dissolved in EtOAc (50 mL) and washed with water (20 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude material, which was purified by reverse phase HPLC to yield N-(5-(2-(2,8-dimethyl-3,4- dihydro-lH-pyrido[4,3-b]indol-5(2H)-yl)phenyl)pyridin-2-yl)acetamide as a TFA salt. 1H NMR (TFA salt, CD3OD) d (ppm): 7.8-8.0 (m, 2H), 7.6-7.78 (m, 3H), 7.35-7.48 (m, 2H), 7.27 (s, 1H), 7.0 (d, 1H), 6.9 (d, 1H), 4.63 (d, 1H), 4.3 (d, 1H), 3.64 (m, 1H), 3.42 (m, 1H), 2.92-3.1 (m, 4H), 2.8 (m, 1H), 2.4 (s, 3H), 2.1 (s, 3H).
With potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 0.75h; 83 Example No. 83: Preparation of Compound No. 83[0371] To a de-aerated solution of 5-(2-bromophenyl)-2,8-dimethyl-2,3,4,5-tetrahydro-lH- pyrido[4,3-b]indole (100 mg, 0.281 mmol), 2-acetamidopyridine-5-boronic acid pinacol ester (147 mg, 0.562 mmol) and K2C03 (116 mg, 0.845 mmol) in DME (4 mL)-water (2 mL) was added Pd(PPh3)4 (16 mg, 0.013 mmol). The reaction mixture was stirred at 90 °C for 45 min. The reaction mixture was concentrated under reduced pressure to dryness. The residue was dissolved in EtOAc (50 mL) and washed with water (20 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude material, which was purified by reverse phase HPLC to yield N-(5-(2-(2,8-dimethyl-3,4-dihydro-lH- pyrido[4,3-b]indol-5(2H)-yl)phenyl)pyridin-2-yl)acetamide as a TFA salt. 1H NMR (TFA salt, CD3OD) δ (ppm): 7.8-8.0 (m, 2H), 7.6-7.78 (m, 3H), 7.35-7.48 (m, 2H), 7.27 (s, IH), 7.0 (d, IH), 6.9 (d, IH), 4.63 (d, IH), 4.3 (d, IH), 3.64 (m, IH), 3.42 (m, IH), 2.92-3.1 (m, 4H), 2.8 (m, IH), 2.4 (s, 3H), 2.1 (s, 3H).
  • 11
  • [ 904326-87-0 ]
  • [ 1332450-87-9 ]
  • [ 1332448-42-6 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In 1,2-dimethoxyethane; water for 0.75h; Inert atmosphere; Reflux; 56 Example No. 56; Preparation of Compound No. 56[0353] To a solution of 5-(4-bromothiophen-3-yl)-2,8-dimethyl-2,3,4,5-tetrahydro-lH- pyrido[4,3-b]indole (100 mg, 0.25 mmol) in DME (2 mL) were added water (1 mL) and K2C03 (110 mg, 0.77 mmol) and purged the solution with N2. Pd(PPh3)4 (20 mg, 0.017 mmol) and 2-acetamidopyridine-5-boronic acid pinacol ester (140 mg, 0.515 mmol) were added to the reaction mixture, which was refluxed under N2 for 45 min. The reaction mixture was cooled to RT and diluted with EtOAc. Aqueous layer was extracted with EtOAc (3x6 mL) and the combined organic layer dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to afford crude material, which was purified by reverse phase HPLC. 1H NMR (TFA salt, CD3OD) d (ppm): 8.0 (s, IH), 7.8 (m, 2H), 7.68 (m, IH), 7.51 (m, IH), 7.33 (s, IH), 6.82-7.0 (m, 2H), 4.77 (d, IH), 4.4 (d, IH), 3.78 (m, IH), 3.5 (m, IH), 3.1 (m, 4H), 2.7 (m, IH), 2.4 (s, 3H), 2.2 (s, 3H).
With potassium carbonate In 1,2-dimethoxyethane; water for 0.75h; Inert atmosphere; 56 Example No. 56: Preparation of Compound No. 56[0344] To a solution of 5-(4-bromothiophen-3-yl)-2,8-dimethyl-2,3,4,5-tetrahydro- 1H- pyrido[4,3-b]indole (100 mg, 0.25 mmol) in DME (2 mL) were added water (1 mL) and K2C03 (110 mg, 0.77 mmol) and purged the solution with N2. Pd(PPh3)4 (20 mg, 0.017 mmol) and 2- acetamidopyridine-5-boronic acid pinacol ester (140 mg, 0.515 mmol) were added to the reaction mixture, which was refluxed under N2 for 45 min. The reaction mixture was cooled toRT and diluted with EtOAc. Aqueous layer was extracted with EtOAc (3x6 mL) and the combined organic layer dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to afford crude material, which was purified by reverse phase HPLC. 1H NMR(TFA salt, CD3OD) δ (ppm): 8.0 (s, IH), 7.8 (m, 2H), 7.68 (m, IH), 7.51 (m, IH), 7.33 (s, IH),6.82-7.0 (m, 2H), 4.77 (d, IH), 4.4 (d, IH), 3.78 (m, IH), 3.5 (m, IH), 3.1 (m, 4H), 2.7 (m, IH),2.4 (s, 3H), 2.2 (s, 3H).
  • 12
  • [ 904326-87-0 ]
  • [ 1332450-87-9 ]
  • [ 1332448-76-6 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In 1,2-dimethoxyethane; water for 0.75h; Inert atmosphere; Reflux; 73 Example No. 73; Preparation of Compound No. 73[0370] To a solution of 5-(4-bromothiophen-3-yl)-2,8-dimethyl-2,3,4,5-tetrahydro- 1H- pyrido[4,3-b]indole (100 mg, 0.276 mmol) in DME-water (2: 1) was added K2C03 (110 mg, 0.77 mmol) and the solution purged with N2. Pd(PPh3)4 (20 mg, 0.017 mmol) and N-methyl- 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide (145 mg, 0.552 mmol) were added to the reaction mixture, which was refluxed under N2 for 45 min. The reaction mixture was cooled to RT and extracted with EtOAc. The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude material, which was purified by reverse phase HPLC. 1H NMR (TFA salt, CD3OD) d (ppm): 8.1-8.27 (m, IH), 8.0 (s, IH), 7.8 (m, 2H), 7.42 (m, IH), 7.3 (s, IH), 6.9-7.0 (m, 2H), 4.76 (d, IH), 4.38 (d, IH), 3.7 (m, IH), 3.5 (m, IH), 3.0 (m, 4H), 2.88 (s, 3H), 2.93 (m, IH), 2.4 (s, 3H).
  • 13
  • [ 904326-87-0 ]
  • [ 1332450-89-1 ]
  • [ 1332448-20-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In water; N,N-dimethyl-formamide at 90℃; for 0.75h; Inert atmosphere; 45 Example No. 45; Preparation of Compound No. 45[0342] To a de-aerated solution of 5-(3-bromophenyl)-2,8-dimethyl-2,3,4,5-tetrahydro-lH- pyrido[4,3-b]indole (100 mg, 0.281 mmol), 2-acetamidopyridine-5-boronic acid pinacol ester (147 mg, 0.560 mmol) and K2C03 (120 mg, 0.845 mmol) in DME (4 mL)-water (2 mL) was added Pd(PPh3)4 (16 mg, 0.013 mmol). The reaction mixture was stirred at 90 °C for 45 min. The solvent was removed under reduced pressure, residue diluted with water (20 mL) and extracted with EtOAc (50 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to obtain crude, which was purified by reverse phase HPLC to yield N-(5-(3-(2,8-dimethyl-3,4-dihydro-lH-pyrido[4,3-b]indol-5(2H)- yl)phenyl)pyridin-2-yl)acetamide. 1H NMR (TFA salt, CD3OD) d (ppm): 8.6 (s, 1H), 8.18 (s, 2H), 7.8 (d, IH), 7.62-7.77 (m, 2H), 7.42 (d, IH), 7.3 (s, IH), 7.17 (d, IH), 7.03 (d, IH), 4.7 (d, IH), 4.42 (d,lH), 3.8 (m, IH), 3.58 (m, IH), 3.0-3.2 (m, 5H), 2.41 (s, 3H), 2.2 (s, 3H).
With potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 0.75h; 45 Example No. 45: Preparation of Compound No. 45[0333] To a de-aerated solution of 5-(3-bromophenyl)-2,8-dimethyl-2,3,4,5-tetrahydro-lH- pyrido[4,3-b]indole (100 mg, 0.281 mmol), 2-acetamidopyridine-5-boronic acid pinacol ester (147 mg, 0.560 mmol) and K2C03 (120 mg, 0.845 mmol) in DME (4 mL)-water (2 mL) was added Pd(PPh )4 (16 mg, 0.013 mmol). The reaction mixture was stirred at 90 °C for 45 min. The solvent was removed under reduced pressure, residue diluted with water (20 mL) and extracted with EtOAc (50 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to obtain crude, which was purified by reverse phase HPLC to yield N-(5-(3-(2,8-dimethyl-3,4-dihydro-lH-pyrido[4,3-b]indol-5(2H)-yl)phenyl)pyridin-2- yl)acetamide. 1H NMR (TFA salt, CD3OD) δ (ppm): 8.6 (s, 1H), 8.18 (s, 2H), 7.8 (d, 1H), 7.62- 7.77 (m, 2H), 7.42 (d, 1H), 7.3 (s, 1H), 7.17 (d, 1H), 7.03 (d, 1H), 4.7 (d, 1H), 4.42 (d,lH), 3.8 (m, 1H), 3.58 (m, 1H), 3.0-3.2 (m, 5H), 2.41 (s, 3H), 2.2 (s, 3H).
  • 14
  • [ 904326-87-0 ]
  • [ 1332450-89-1 ]
  • [ 1332448-80-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 0.75h; Inert atmosphere; 75 Example No. 75; Preparation of Compound No. 75[0372] To a degassed solution of 5-(3-bromophenyl)-2,8-dimethyl-2,3,4,5-tetrahydro-lH- pyrido[4,3-b]indole (101 mg, 0.286 mmol), N-methyl-5-(4,4,5,5-tetramethyl- 1,3,2- dioxaborolan-2-yl)picolinamide (150 mg, 0.57 mmol) and K2C03 (236 mg, 1.71 mmol) in DME- water (2: 1) was added Pd(PPh3)4 (33 mg, 0.028 mmol). The reaction mixture was stirred at 90 °C for 45 min. The reaction mixture concentrated under reduced pressure. The residue was dissolved in EtOAc (50 mL) and washed with water (20 mL). The organic layer dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude material, which was purified by reverse phase HPLC to yield 5-(3-(2,8-dimethyl-3,4-dihydro- lH-pyrido[4,3-b]indol-5(2H)-yl)phenyl)-N-methylpicolinamide. 1H NMR (TFA salt, CD3OD) d (ppm): 8.97 (s, 1H), 8.23 (d, 1H), 8.12 (d, 1H), 7.85 (d, 1H), 7.78 (m, 2H), 7.5 (d, 1H), 7.37 (s, 1H), 7.21 (d, 1H), 7.04 (d, 1H), 4.76 (m, 1H), 4.4 (m, 1H), 3.8 (m, 1H), 3.6 (m, 1H), 3.08-3.21 (m, 5H), 3.0 (s, 3H), 2.4 (s, 3H).
  • 15
  • [ 904326-87-0 ]
  • [ 1332450-92-6 ]
  • [ 1332449-35-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 2h; Inert atmosphere; 105 Example No. 105Preparation of Compound No. 139[0402] To a de-aerated solution of 5-(5-bromopyridin-2-yl)-2,8-dimethyl-2,3,4,5- tetrahydro-lH-pyrido[4,3-b]indole (100 mg, 0.280 mmol), 2-acetamidopyridine-5-boronic acid pinacol ester (146 mg, 0.557 mmol) and K2C03 (116 mg, 0.839 mmol) in DME (4 mL) and water (2 mL) was added Pd(PPh3)4 (16 mg, 0.013 mmol). The reaction mixture was stirred at 90 °C for 2h. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water (30 mL) and extracted with EtOAc (50 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to afford crude material, which was purified by reverse HPLC to yield N-(6'-(2,8-dimethyl-3,4- dihydro-lH-pyrido[4,3-b]indol-5(2H)-yl)-3,3'-bipyridin-6-yl)acetamide as the TFA salt. 1H NMR (CD3OD, TFA salt) d (ppm): 8.9 (s, IH), 8.63 (s, IH), 8.3 (d, IH), 8.22 (d, IH), 8.18 (d, IH), 7.76 (d, IH), 7.5 (d, IH), 7.38 (s, IH), 7.13 (d, IH), 4.7 (d, IH), 4.4 (d, IH), 3.82 (bs, IH), 3.42-3.6 (m, 3H), 3.18 (s, 3H), 2.42 (s, 3H), 2.2 (s, 3H).
With potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 2h; 105 Example No. 105: Preparation of Compound No. 139 . . + | 03 j ιο a ae-aerated solution or ^-(S-bromopyridin-z-ylj-z^-dimetnyi-z ^ -ieiranydro- lH-pyrido[4,3-b]indole (100 mg, 0.280 mmol), 2-acetamidopyridine-5-boronic acid pinacol ester (146 mg, 0.557 mmol) and K2C03 (116 mg, 0.839 mmol) in DME (4 mL) and water (2 mL) was added Pd(PPh )4 (16 mg, 0.013 mmol). The reaction mixture was stirred at 90 °C for2h. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water (30 mL) and extracted with EtOAc (50 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to afford crude material, which was purified by reverse HPLC to yield N-(6'-(2,8-dimethyl-3,4-dihydro-lH-pyrido[4,3-b]indol-5(2H)-yl)-3,3'-bipyridin-6-yl)acetamide as the TFA salt. 1H NMR (CD3OD, TFA salt) δ (ppm):8.9 (s, IH), 8.63 (s, IH), 8.3 (d, IH), 8.22 (d, IH), 8.18 (d, IH), 7.76 (d, IH), 7.5 (d, IH), 7.38(s, IH), 7.13 (d, IH), 4.7 (d, IH), 4.4 (d, IH), 3.82 (bs, IH), 3.42-3.6 (m, 3H), 3.18 (s, 3H), 2.42(s, 3H), 2.2 (s, 3H).
  • 16
  • N-[(3S,3aS)-7-bromo-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl}acetamide [ No CAS ]
  • [ 904326-87-0 ]
  • [ 1341208-75-0 ]
YieldReaction ConditionsOperation in experiment
35.3% With potassium fluoride; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 80℃; for 2h;
  • 17
  • [ 904326-87-0 ]
  • [ 1354288-75-7 ]
  • [ 1354287-95-8 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; tricyclohexylphosphine In 1,4-dioxane; water at 90℃; for 19h; Inert atmosphere; 167 5,7-Difluoro-N-(5-iodo-2-morpholinopyridin-4-yl)-3-methyl-2-(pyridin-2-yl)- quinolin-4-amine (94 mg, 0.17 mmol), 2-acetamidopyridine-5-boronic acid pinacol ester (89 mg, 0.34 mmol), tricyclohexylphosphine (10 mg, 0.037 mmol), and tris(dibenzylideneacetone)dipalladium (0) (16 mg, 0.018 mmol) were added to a flask then degassed and backfilled with argon. To the flask, 1 ,4-dioxane (2.5 mL) and aq. 1.3 M potassium phosphate tribasic (0.33 mL, 0.43 mmol) were added by syringe. The resulting reaction was heated to 90 °C and monitored with TLC and LC-MS. After 19 h, the reaction was cooled to rt then poured into water. After extracting twice with EtOAc and twice with DCM, the combined organic extractions were dried over anhydrous magnesium sulfate. After filtration and concentration, the residue was purified on silica gel (0-65 % of a premixed solution of 89:9: 1 DCM: MeOH: ammonium hydroxide in DCM) to afford a film that was further purified with HPLC (5-90% of 0.1% TFA acetonitrile solution in 0.1% TFA water solution.) The desired fractions were concentrated then diluted with EtOAc. After washing twice with saturated aq. sodium bicarbonate solution and once with brine, the solvent was removed under reduced pressure to yield a light yellow solid that was purified using SFC to afford a faint yellow solid as N- (4'-(5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-ylamino)-6'-morpholino- 3,3*-bipyridin-6-yl)acetamide. 1H NMR (500 MHz, DMSO-d6) δ ppm 10.53 (1 H, s), 8.74 (1 H, m), 8.30 (1 H, d, J=2.4 Hz), 8.13 (3 H, m), 7.87 (1 H, d, J=7.8 Hz), 7.82 (1 H, s), 7.77 (1 H, dd, J=8.6, 2.2 Hz), 7.63 (1 H, dd, J=9.7, 2.1 Hz), 7.52 (1 H, ddd, J=7.6, 4.9, 1.0 Hz), 7.46 (1 H, ddd, J=12.5, 9.5, 2.4 Hz), 5.63 (1 H, s), 3.67 (4 H, m), 3.28 (4 H, m), 2.25 (3 H, s), 2.10 (3 H, s). Mass Spectrum (pos.) m/e: 568.2 (M+H)+.
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