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[ CAS No. 263270-02-6 ]

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Chemical Structure| 263270-02-6
Chemical Structure| 263270-02-6
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CAS No. :263270-02-6 MDL No. :MFCD07367903
Formula : C10H12BrNO2 Boiling Point : 279.8°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :258.11 g/mol Pubchem ID :-
Synonyms :

Safety of [ 263270-02-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P301+P312-P330 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 263270-02-6 ]

  • Downstream synthetic route of [ 263270-02-6 ]

[ 263270-02-6 ] Synthesis Path-Downstream   1~25

  • 1
  • [ 263270-02-6 ]
  • [ 7486-35-3 ]
  • 5-vinyl-nicotinic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride; 2,6-di-tert-butyl-4-methyl-phenol; lithium chloride In N,N-dimethyl-formamide at 70℃;
  • 2
  • [ 263270-02-6 ]
  • 5-[2-(4-hydroxy-2,6-dimethyl-phenyl)-vinyl]-nicotinic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: LiCl; Pd(PPh3)2Cl2; BHT / dimethylformamide / 70 °C 2: Pd2dba3; TEA; P(o-tol)3 / dimethylformamide / 95 °C
  • 3
  • [ 263270-02-6 ]
  • 5-[2-(2,6-dimethyl-4-methylcarbamoyloxy-phenyl)-vinyl]-nicotinic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: LiCl; Pd(PPh3)2Cl2; BHT / dimethylformamide / 70 °C 2: Pd2dba3; TEA; P(o-tol)3 / dimethylformamide / 95 °C 3: dimethylformamide
  • 4
  • [ 20826-04-4 ]
  • [ 24424-99-5 ]
  • [ 263270-02-6 ]
YieldReaction ConditionsOperation in experiment
96% With dmap In tetrahydrofuran Reflux;
91% With 4-pyrrolidin-1-ylpyridine; triethylamine In tetrahydrofuran at 20℃; for 48h; 1 Example 1; Tert-Butyl 5-bromonicotinate To a mixture of 5-bromonicotinic acid (0. 30g, 1. 49mmol) and di-tert-butyldicarbonate (0. 45g, 2. 06mmol) in THF (15mL) was added triethylamine (0. 25mL, L79mmol) followed by 4- (PYRROLIDINO) PYRIDINC (3OMG, O. 20MMOL). T'HE RESULTANT SOLUTION was stirred at ambient temperature FOR 48 HE. THE VOLATILCS WERE THEN removed under vacuum and the residue was purified by column chromatography on silica (gradient, CH2Cl2 to 3% MEOH/CH2Cl2) TO PROVIDE the product as a white solid (0. 35g, 91%) 1H-n.m. r. (CDCL3) #1. 60 (s, 9H, t-butyl), 8.35 (m, 1H, Ar), 8.79 (d, J2.5 Hz, 1H, Ar), 9. 06 (D, 1.4 Hz, 1H, Ar).
91.07% With dmap In tetrahydrofuran at 25℃; for 12h; 5-(cyclobutylamino)nicotinic acid tert-butyl 5-bromonicotinate. Di-tert-butyl dicarbonate (7.72 g, 35.40 mmol, 8.12 mL) was added to a stirred mixture of 5-bromopyridine-3-carboxylic acid (5.5 g, 27.23 mmol) and N,N-dimethylpyridin-4-amine (1.66 g, 13.61 mmol) in THF (100 mL) at 25° C. The reaction mixture was stirred at 25° C. for 12 hr, and evaporated in vacuo. The residue was dissolved in dichloromethane (100 ml) and washed successively with aqueous sodium hydrogen sulphate (1.80 g, 14.97 mmol) solution (40 ml), and water (50 ml). The organic layer was separated, dried over sodium sulphate and evaporated in vacuo to afford tert-butyl-5-bromopyridine-3-carboxylate (6.4 g, 24.80 mmol, 91.07% yield) as white solid. 1H NMR (500 MHz, CDCl3) δ (ppm) 1.61 (s, 9H), 8.36 (t, 1H), 8.81 (d, 1H), 9.07 (d, 1H). LCMS(ESI): [M+H]+ m/z: 258.1 calcd; found 259.0; Rt=1.508 min.
82% With dmap In tetrahydrofuran at 20℃; for 1.5h; Cooling with ice; Tert-butyl 5-bromopyridine-3-carboxylate Boc20 (4.28 g, 19.6 mmol) in THF (40 ml) was added to an ice-cold solution of 5-bromonicotinic acid (3.6 g, 17.82 mmol) and DMAP (1.09 g, 8.91 mmol) in THF (70 ml). The reaction mixture was stirred and allowed to warm to room temperature over 1.5 h then concentrated in vacuo. The residue was dissolved in saturated NaHC03 (aq) and extracted with DCM (3 x 100 ml). The combined organic extracts were dried (Na2S04), filtered and evaporated in vacuo. Purification by flash column chromatography (eluting with a gradient of 0-10% EtOAc / heptane) afforded the title compound (3.79 g, 82%) as a coloirless oil which solidified over time. 1 H-NMR (CDCI3, 250 MHz): d[ppm]= 9.09 (m, 1 H), 8.83 (d, J = 2.2 Hz, 1 H), 8.38 (t, J = 2.2 Hz, 1 H), 1.63 (s, 9H) HPLCMS (Method M): [m/z]: 259.85 / 261.85 [M+H]+
79% With dmap In tetrahydrofuran for 1h; Reflux;

  • 5
  • [ 263270-02-6 ]
  • [ 94839-07-3 ]
  • [ 713519-86-9 ]
YieldReaction ConditionsOperation in experiment
88% With potassium carbonate;palladium 10% on activated carbon; In water; N,N-dimethyl-formamide; at 90℃; for 15h; in a flask was placed tert-butyl 5-bromonicotinate (1.00g, 3.87mmol), 10% w/w palladium on carbon (210mg, 30.2mmol pd), potassium carbonate (1.10g, 7.96mmol), 3, 4- methylcnedioxy-phenyl boronic acid (0. 96g, 5. 79mmol), dimethylformamide (50ml) and water (250l). the flask was purged with nitrogen and then heated, with stirring, to 90c for 15hr. the reaction mixture was allowed to cool, diluted with water (350inl) and extracted with chzcl2 (4x). the combined extracts was washed with water, dried (mgso4) and concentrated in vacuo. the crude residue was purified by flash chromatography on silica (gradient, ch2cl2 to 50% ether / ch2cl2) to provide an off-white solid (1. 02g, 88%). 1h-n.m.r. (cdcl3) #1.63 (s, 9h, t-butyl), 6.04 (s, 2h, ch2), 6. 90 (m, 1h, ar), 7. 08 (m, 2h, ar), 8. 34 (rn, 1h, ar), 8. 89 (d, j1.9 hz, 1h, ar), 9.09 (d, j2.0 hz, 1h, ar).
  • 6
  • [ 20826-04-4 ]
  • [ 75-65-0 ]
  • [ 263270-02-6 ]
YieldReaction ConditionsOperation in experiment
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 20℃; 14 Reference Example 14: 5-Bromo-nicotinic acid tert-butyl ester. 5-Bromo-nicotinic acid (20.2g, lOOmmol) was dissolved in CHCI3 (200 mL) and tert-BuOR (40 mL); and WSC (21. Ig, 1 lOmmol) andDMAP (21. Ig, 1 lOmmol) was added thereto in order, and stirred at room temperature over night. The reaction mixture was diluted with chloroform, washed with 0.5N HCl aq. (220 mL), 0.5N NaOH aq. (100 mL), brine and dried over MgSO4 and silica gel. After filtration, the solvents were removed in vacuo to afford 5-Bromo-nicotinic acid fer^-butyl ester as a colorless solid. This solid was used for the next step without further purification.
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In chloroform at 20℃; 19 REFERENCE EXAMPLE 19 5-Bromo-nicotinic acid tert-butyl ester 5-Bromo-nicotinic acid (20.2 g, 100 mmol) was dissolved in CHCl3 (200 mL) and tert-BuOH (40 mL); and WSC (21.1 g, 110 mmol) and DMAP (21.1 g, 10 mmol) was added thereto in order, and stirred at room temperature over night. The reaction mixture was diluted with chloroform, washed with 0.5N HCl aq. (220 mL), 0.5N NaOH aq. (100 mL), brine and dried over MgSO4 and silica gel. After filtration, the solvents were removed in vacuo to afford 5-Bromo-nicotinic acid tert-butyl ester as a colorless solid.
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 20℃; 5 5-Bromo-nicotinic acid (20.2g, lOOmmol) was dissolved in CHCI3 (200 mL) and tert-BuOH (40 mL); and WSC-HCl (21. Ig, 1 lOmmol) and DMAP (21. Ig, 1 lOmmol) was added thereto in order, and stirred at room temperature over night. The reaction mixture was diluted with chloroform, washed with 0.5N HCl aq. (220 mL), 0.5N NaOH aq. (100 mL), brine and dried over MgSO4 and silica gel. After filtration, the solvents were removed in vacuo to afford 5-Bromonicotinic acid tert-butyl ester as a colorless solid. This solid was used for the next step without further purification.
  • 7
  • [ 263270-02-6 ]
  • [ 690632-38-3 ]
  • [ 921760-55-6 ]
YieldReaction ConditionsOperation in experiment
Reference Example 15: 5-11 '-/er/-butoxycarbonyl]-4-oxospiro[chroman-2.4'-piperidin]-6-yllnicotinic acid tert-butyl ester, ^ert-butyl--bromo^-oxospirofchroman^^'-piperidinej-l'-carboxylate (19.8 g, 50.0 mmol), bis(pinacolato)diboran (14.0 g, 55.0 mmol), Pd(OAc)2 (560 mg, 2.50 mmol), DPPF (2.77 g, 5.00 mmol), and AcOK (5.82 g, betaO.Ommol) were suspended in dioxane (250 mL) and heated at 1000C for 10 hours. After cooling down to room temperature, 5-bromo-nicotinicacid tert-butyl ester (14.2g, 55.0 mmol), Pd(PPh3)4 (5.78g, 5.00 mmol) and 2M Na2CO3 aq. (125 mL, 250mmol) were added to the reaction mixture; and then heated at 1000C for 15 hours. The reaction mixture was diluted with EtOAc and H2O, organic layer was washed with brine and dried over MgSOphi After filtration, the solvents were removed in vacuo and the residue was purified by silica gel column chromatography (hexane/EtOAc = 10/0 to 6/4) and the obtained brown solid was crystallized from EtOAc/hexane (1/1) to afford 5-{l'-ter/- butoxycarbonyl]-4-oxospiro[chroman-2,4'-piperidin]-6-yl} nicotinic acid tert-butyl ester as a pale yellow solid.
  • 8
  • [ 263270-02-6 ]
  • [ 921760-66-9 ]
  • [ 921760-55-6 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In 1,4-dioxane; water at 100℃; for 15h; 20 REFERENCE EXAMPLE 20 5-{1'-tert-butoxycarbonyl]-4-oxospiro[chroman-2,4'-piperidin]-6-yl}nicotinic acid tert-butyl ester tert-butyl-6-bromo-4-oxospiro[chroman-2,4'-piperidine]-1'-carboxylate (19.8 g, 50.0 mmol), bis(pinacolato)diboran (14.0 g, 55.0 mmol), Pd(OAc)2 (560 mg, 2.50 mmol), DPPF (2.77 g, 5.00 mmol), and AcOK (5.82 g, 60.0 mmol) were suspended in dioxane (250 mL) and heated at 100° C. for 10 hours. After cooling down to room temperature, 5-bromo-nicotinic acid tert-butyl ester (14.2 g, 55.0 mmol), Pd(PPh3)4 (5.78 g, 5.00 mmol) and 2M Na2CO3 aq. (125 mL, 250 mmol) were added to the reaction mixture; and then heated at 100° C. for 15 hours. The reaction mixture was diluted with EtOAc and H2O, organic layer was washed with brine and dried over MgSO4. After filtration, the solvents were removed in vacuo and the residue was purified by silica gel column chromatography (hexane/EtOAc=10/0 to 6/4) and the obtained brown solid was crystallized from EtOAc/hexane (1/1) to afford 5-{1'-tert-butoxycarbonyl]-4-oxospiro[chroman-2,4'-piperidin]-6-yl}nicotinic acid tert-butyl ester as a pale yellow solid.
With sodium carbonate In 1,4-dioxane at 100℃; for 15h; 6 Tert-butyl 6-bromo-4-oxospiro[chroman-2,4'-piperidine]-r-carboxylate (19.8 g, 50.0 mmol), bis(pinacolato)diboran (14.0 g, 55.0 mmol), Pd(OAc)2 (560 mg, 2.50 mmol), DPPF (2.77 g, 5.00 mmol), and AcOK (5.82 g, O.Ommol) were suspended in dioxane (250 mL) and heated at 1000C for 10 hours. After cooling down to room temperature, 5-bromo-nicotinicacid tert-butyl ester (14.2g, 55.0 mmol), Pd(PPh3)4 (5.78g, 5.00 mmol) and 2M Na2CO3 aq. (125 mL, 250mmol) were added to the reaction mixture; and then heated at 1000C for 15 hours. The reaction mixture was diluted with EtOAc and H2O, organic layer was washed with brine and dried over MgSOφ After filtration, the solvents were removed in vacuo and the residue was purified by silica gel column chromatography (hexane/EtOAc = 10/0 to 6/4) and the obtained brown solid was crystallized from EtOAc/hexane (1/1) to afford 5-{r-tert-butoxycarbonyl-4-oxospiro[chroman- 2,4'-piperidin]-6-yl} nicotinic acid tert-butyl ester as a pale yellow solid.
  • 9
  • [ 263270-02-6 ]
  • [ 557-21-1 ]
  • [ 887579-69-3 ]
YieldReaction ConditionsOperation in experiment
With zinc In N,N-dimethyl acetamide at 120℃; for 1.5h; 103 Instead of the starting material of Reference Example 56, that is, the compound S55, the 5-bromonicotinic acid was used for the similar procedure as in Reference Example 56. To the obtained tert-butyl 5-bromonicotinate (22.4 g), dimethylacetoamide (112 ml), tris(dibenzylideneacetone)dipalladium (1.59 g), zinc cyanide (6.1 g), diphenylphosphinoferrocene (1.92 g), and zinc powder (0.68 g) were added and the mixture was stirred under argon atmosphere at 120°C for 1.5 hours. The reaction solution was filtered by sellite, which was then washed with ethyl acetate, and the filtrate was washed with saturated saline. The organic layer was dried over with anhydrous sodium sulfate, then concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to obtain tert-butyl 5-cyanonicotinate (13.1 g).
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); zinc In N,N-dimethyl acetamide at 120℃; for 3h; Inert atmosphere; General procedure: To 6-chloronicotinic acid 19a (10 g) in methylene chloride(100 ml) solution, N,N’-diisopropyl-O-tert-butylisourea (50 g) wasadded and the mixture was stirred under heating and reflux for16 h. The insoluble compound was filtered out, and the filtratewas concentrated. The residue was purified by silica gel column chromatography (chloroform/ethyl acetate = 6/1) to obtain the compound 20a (11.66 g). To the compound 20a (6.0 g) in dimethylacetoamide (30 ml) solution, tris(dibenzylideneacetone)dipalladium (0.51 g), zinc cyanide (0.22 g), diphenylphosphinoferrocene (0.62 g), and zinc powder (1.98 g) were added and the mixture was stirred under argon atmosphere at 120 °C for 3 h. The reaction solution was filtered by sellite, which was then washed with ethyl acetate. Then, the filtrate was washed with distilled water and saturated saline, then the organic layer was dried over with anhydrous sodium sulfate and concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate= 5/1) to obtain the compound 21a (3.59 g). To copper(I) iodide(0.93 g) in tetrahydrofuran (50 ml) suspension, ethylmagnesium bromide (0.86 M tetrahydrofuran solution)(12.5 ml) was added dropwise under cooling at 0 °C, the mixture was stirred at 0 °C for 30 min, then the compound 21a (1.0 g) obtained above in tetrahydrofuran (10 ml) solution was added atthe 20 °C. After stirring for 30 min at that temperature, 28% ammonia solution in water and ethyl acetate were added to the mixture and the solution separated. The aqueous layer was extracted with ethyl acetate, while the combined organic layer was washed with saturated saline, then was dried over with anhydrous sodium sulfate and concentrated. The obtained residue was purifiedby silica gel column chromatography (hexane/ethyl acetate= 8/1) to obtained the compound 22a (0.47 g). To the compound 22a (200 mg) in tetrahydrofuran (1 ml) solution, (-)-B-chlorodiisopinocampheylborane (65% hexane solution) (0.92 ml) was added dropwise under cooling at 20 °C, then the mixture was stirred at that temperature for 18 h. Then, ether and distilled water were added to the reaction mixture, and the solution was separated. The organic layer was extracted with distilled water and 1 M hydrogen chloride. Then, the combined aqueous layer was neutralized by sodium hydrogen carbonate, and extracted with ethyl acetate. Organic layer was washed with saturated saline, then was dried over with anhydrous sodium sulfate and concentrated to obtained the title compound (150 mg, 84% ee). The optical purity was determined using CHIRALCEL AD-H(Daicel Chemical Industries) (movement phase: hexane/ethanol= 98/2, 1.0 ml/min).
  • 10
  • [ 263270-02-6 ]
  • [ 73183-34-3 ]
  • [ 1309982-38-4 ]
YieldReaction ConditionsOperation in experiment
With 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate In 1,4-dioxane at 100℃; 2-6 Reference Example 2-6:[S-ftert-ButoxycarbonvDpyridin-S-yliboronic acidPd(OAc)2 (0.112 g, 0.500 mmol), DPPF (0.554 g, 1.000 mmol), KOAc (1.18 g, 12.0 mmol), tert-butyl 5-bromonicotinate (2.58 g, 10.0 mmol) and bis(pinacolato)diboran (2.79 g, 11.0 mmol) were suspended in 1,4-dioχane (25 ml) and the mixture was stirred at 100°C overnight. The mixture was filtered through celite pad, and the filtrate was evaporated in vacuo. The residue was suspended in acetone (25.0 ml) / H2O (25.0 ml), and sodium periodate (6.41 g,30.0 mmol) and ammonium acetate (2.31 g, 30.0 mmol) were added thereto. The mixture wε. stirred at room temperature for overnight and was diluted with CHCI3 and H2O. The organic layer was washed with H2O, brine, and dried over MgSOφ After flteration and evaporation, the residue was purified by silicagel colunm chromatography (CHCI3 / MeOH) to give intended compound as a brown solid.
  • 11
  • [ 263270-02-6 ]
  • [ 1001755-36-7 ]
YieldReaction ConditionsOperation in experiment
85% With ammonium hydroxide; copper(l) iodide; 4R-4-hydroxyproline In dimethyl sulfoxide at 80℃;
  • 12
  • [ 20826-04-4 ]
  • [ 67098-46-8 ]
  • [ 263270-02-6 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane for 16h; Reflux; General procedure: To 6-chloronicotinic acid 19a (10 g) in methylene chloride(100 ml) solution, N,N’-diisopropyl-O-tert-butylisourea (50 g) wasadded and the mixture was stirred under heating and reflux for16 h. The insoluble compound was filtered out, and the filtratewas concentrated. The residue was purified by silica gel column chromatography (chloroform/ethyl acetate = 6/1) to obtain the compound 20a (11.66 g). To the compound 20a (6.0 g) in dimethylacetoamide (30 ml) solution, tris(dibenzylideneacetone)dipalladium (0.51 g), zinc cyanide (0.22 g), diphenylphosphinoferrocene (0.62 g), and zinc powder (1.98 g) were added and the mixture was stirred under argon atmosphere at 120 °C for 3 h. The reaction solution was filtered by sellite, which was then washed with ethyl acetate. Then, the filtrate was washed with distilled water and saturated saline, then the organic layer was dried over with anhydrous sodium sulfate and concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate= 5/1) to obtain the compound 21a (3.59 g). To copper(I) iodide(0.93 g) in tetrahydrofuran (50 ml) suspension, ethylmagnesium bromide (0.86 M tetrahydrofuran solution)(12.5 ml) was added dropwise under cooling at 0 °C, the mixture was stirred at 0 °C for 30 min, then the compound 21a (1.0 g) obtained above in tetrahydrofuran (10 ml) solution was added atthe 20 °C. After stirring for 30 min at that temperature, 28% ammonia solution in water and ethyl acetate were added to the mixture and the solution separated. The aqueous layer was extracted with ethyl acetate, while the combined organic layer was washed with saturated saline, then was dried over with anhydrous sodium sulfate and concentrated. The obtained residue was purifiedby silica gel column chromatography (hexane/ethyl acetate= 8/1) to obtained the compound 22a (0.47 g). To the compound 22a (200 mg) in tetrahydrofuran (1 ml) solution, (-)-B-chlorodiisopinocampheylborane (65% hexane solution) (0.92 ml) was added dropwise under cooling at 20 °C, then the mixture was stirred at that temperature for 18 h. Then, ether and distilled water were added to the reaction mixture, and the solution was separated. The organic layer was extracted with distilled water and 1 M hydrogen chloride. Then, the combined aqueous layer was neutralized by sodium hydrogen carbonate, and extracted with ethyl acetate. Organic layer was washed with saturated saline, then was dried over with anhydrous sodium sulfate and concentrated to obtained the title compound (150 mg, 84% ee). The optical purity was determined using CHIRALCEL AD-H(Daicel Chemical Industries) (movement phase: hexane/ethanol= 98/2, 1.0 ml/min).
  • 13
  • [ 263270-02-6 ]
  • C37H45ClN4O9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene; zinc / N,N-dimethyl acetamide / 3 h / 120 °C / Inert atmosphere 2.1: copper(l) iodide / tetrahydrofuran / 0.5 h / 0 °C 2.2: 0.5 h / -20 °C 3.1: (-)-diisopinocamphenylborane chloride / tetrahydrofuran; hexane / 18 h / -20 °C 4.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1 h / 0 - 20 °C 5.1: hydrazine hydrate / methanol / 2 h / 60 °C 6.1: ethyl acetate; ethanol 7.1: triethylamine; dmap / N,N-dimethyl-formamide / 20 h / 0 °C
  • 14
  • [ 263270-02-6 ]
  • 5-[(1R)-1-([(6R)-6-(5-chloro-2-methoxybenzyl)-3,7-dioxo-1,4-diazepan-1-yl]carbonyl}amino)propyl]nicotinic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene; zinc / N,N-dimethyl acetamide / 3 h / 120 °C / Inert atmosphere 2.1: copper(l) iodide / tetrahydrofuran / 0.5 h / 0 °C 2.2: 0.5 h / -20 °C 3.1: (-)-diisopinocamphenylborane chloride / tetrahydrofuran; hexane / 18 h / -20 °C 4.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1 h / 0 - 20 °C 5.1: hydrazine hydrate / methanol / 2 h / 60 °C 6.1: ethyl acetate; ethanol 7.1: triethylamine; dmap / N,N-dimethyl-formamide / 20 h / 0 °C 8.1: hydrogenchloride / acetic acid / 14 h / 20 °C
  • 15
  • [ 263270-02-6 ]
  • [ 959750-37-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene; zinc / N,N-dimethyl acetamide / 3 h / 120 °C / Inert atmosphere 2.1: copper(l) iodide / tetrahydrofuran / 0.5 h / 0 °C 2.2: 0.5 h / -20 °C
  • 16
  • [ 263270-02-6 ]
  • C13H19NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene; zinc / N,N-dimethyl acetamide / 3 h / 120 °C / Inert atmosphere 2.1: copper(l) iodide / tetrahydrofuran / 0.5 h / 0 °C 2.2: 0.5 h / -20 °C 3.1: (-)-diisopinocamphenylborane chloride / tetrahydrofuran; hexane / 18 h / -20 °C
  • 17
  • [ 263270-02-6 ]
  • [ 1444199-90-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene; zinc / N,N-dimethyl acetamide / 3 h / 120 °C / Inert atmosphere 2.1: copper(l) iodide / tetrahydrofuran / 0.5 h / 0 °C 2.2: 0.5 h / -20 °C 3.1: (-)-diisopinocamphenylborane chloride / tetrahydrofuran; hexane / 18 h / -20 °C 4.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1 h / 0 - 20 °C
  • 18
  • [ 263270-02-6 ]
  • [ 889856-78-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene; zinc / N,N-dimethyl acetamide / 3 h / 120 °C / Inert atmosphere 2.1: copper(l) iodide / tetrahydrofuran / 0.5 h / 0 °C 2.2: 0.5 h / -20 °C 3.1: (-)-diisopinocamphenylborane chloride / tetrahydrofuran; hexane / 18 h / -20 °C 4.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1 h / 0 - 20 °C 5.1: hydrazine hydrate / methanol / 2 h / 60 °C
  • 19
  • [ 263270-02-6 ]
  • [ 1312771-55-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene; zinc / N,N-dimethyl acetamide / 3 h / 120 °C / Inert atmosphere 2.1: copper(l) iodide / tetrahydrofuran / 0.5 h / 0 °C 2.2: 0.5 h / -20 °C 3.1: (-)-diisopinocamphenylborane chloride / tetrahydrofuran; hexane / 18 h / -20 °C 4.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1 h / 0 - 20 °C 5.1: hydrazine hydrate / methanol / 2 h / 60 °C 6.1: ethyl acetate; ethanol
  • 20
  • [ 263270-02-6 ]
  • [ 2417-72-3 ]
  • tert-butyl 5-(4-(methoxycarbonyl)benzyl)nicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: tert-butyl 5-bromopyridine-3-carboxylate With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; bis(pinacol)diborane In 1,4-dioxane at 85℃; Inert atmosphere; Stage #2: Methyl 4-(bromomethyl)benzoate With sodium carbonate In 1,4-dioxane; water at 80℃; Inert atmosphere; 121 To a solution of tert-butyl 5-bromonicotinate (5.0 g, 19.4 mmol, 1.0 eq) in 1,4-dioxane (200 mL) were added KOAc (5.7 g, 58.2 mmol, 3.0 eq), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (4.93 g, 19.4 mmol, 1.0 eq) and Pd(dppf)Cl2 (355 mg, 0.49 mmol, 0.03 eq). The mixture was heated at 85 °C overnight under N2, and then the mixture was cooled to rt. To the mixture were added methyl 4-(bromomethyl)benzoate (4.44 g, 19.4 mmol, 1.0 eq), Pd(dppf)Cl2 (355 mg, 0.49 mmol, 0.03 eq) and Na2C03 (6.17 g, 58.2 mmol, 3.0 eq) in water (40 mL). The mixture was heated to 80 °C overnight. The mixture was concentrated to dryness under reduced pressure. The residue was mixed with water (100 mL) and extracted with EA (100 mL x 3). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2S04 and concentrated. The residue was purified on silica gel column (PE/EA = 10/1 to 4/1) to afford tert-butyl 5-(4- (methoxycarbonyl)benzyl)nicotinate as a yellow solid (3.8 g, 60%).
  • 21
  • [ 263270-02-6 ]
  • N-((3-chloro-1H-indol-5-yl)methyl)-5-(4-((2-oxopyrazin-1(2H)-yl)methyl)benzyl)nicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: bis(pinacol)diborane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 85 °C / Inert atmosphere 1.2: 80 °C / Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran / -78 - 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 20 °C 4.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 20 °C 5.1: thionyl chloride / dichloromethane / 20 °C / Cooling with ice 6.1: potassium carbonate / acetonitrile / 2 h / 80 °C
  • 22
  • [ 263270-02-6 ]
  • 5-(4-(hydroxymethyl)benzyl)nicotinic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: bis(pinacol)diborane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 85 °C / Inert atmosphere 1.2: 80 °C / Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran / -78 - 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 20 °C
  • 23
  • [ 263270-02-6 ]
  • N-((3-chloro-1H-indol-5-yl)methyl)-5-(4-(hydroxymethyl)benzyl)nicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: bis(pinacol)diborane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 85 °C / Inert atmosphere 1.2: 80 °C / Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran / -78 - 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 20 °C 4.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 20 °C
  • 24
  • [ 263270-02-6 ]
  • N-((3-chloro-1H-indol-5-yl)methyl)-5-(4-(chloromethyl)benzyl)nicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: bis(pinacol)diborane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 85 °C / Inert atmosphere 1.2: 80 °C / Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran / -78 - 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 20 °C 4.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 20 °C 5.1: thionyl chloride / dichloromethane / 20 °C / Cooling with ice
  • 25
  • [ 263270-02-6 ]
  • N-((5-chloro-1H-indazol-3-yl)methyl)-5-(4-((2-oxopyrazin-1(2H)-yl)methyl)benzyl)nicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: bis(pinacol)diborane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 85 °C / Inert atmosphere 1.2: 80 °C / Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran / -78 - 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 20 °C 4.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 4.2: 2 h / 20 °C / Inert atmosphere 5.1: thionyl chloride; triethylamine / dichloromethane / 2 h / 0 - 20 °C 6.1: potassium carbonate / acetonitrile / 18 h / Reflux 7.1: hydrogenchloride / methanol; ethyl acetate / 3 h / 40 °C
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