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CAS No. : | 1354050-38-6 | MDL No. : | MFCD22192498 |
Formula : | C9H9BrO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HNUALSDMDHKUEH-UHFFFAOYSA-N |
M.W : | 245.07 | Pubchem ID : | 70699611 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 52.51 |
TPSA : | 35.53 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.36 cm/s |
Log Po/w (iLOGP) : | 2.18 |
Log Po/w (XLOGP3) : | 2.02 |
Log Po/w (WLOGP) : | 2.28 |
Log Po/w (MLOGP) : | 1.54 |
Log Po/w (SILICOS-IT) : | 2.67 |
Consensus Log Po/w : | 2.14 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.78 |
Solubility : | 0.411 mg/ml ; 0.00168 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.39 |
Solubility : | 0.99 mg/ml ; 0.00404 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.46 |
Solubility : | 0.085 mg/ml ; 0.000347 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.62 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With aluminum (III) chloride; sodium iodide; In dichloromethane; acetonitrile; at 0 - 20℃; for 5h; | A solution of <strong>[1354050-38-6]4-bromo-2,6-dimethoxybenzaldehyde</strong> (10 g, 40.8 mmol) and sodium iodide (12.2 g, 81.6 mmol) in MeCN/DCM (50 mL, 1 : 1) was cooled to 0 C. AlCl3 (10.8 g, 81.6 mmol) was added slowly. The reaction was stirred at rt for 5 h and TLC showed the reaction was complete. The mixture was poured into sat. ammonium chloride and extracted with ethyl acetate (100 mLx3). The organic extracts were combined, washed with brine (50 mLx2), dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate =300: 1 to 200: 1) to give the desired product and its iodo-substitution compound (6.3 g, 67% yield). LC-MS m/z [M+H]+ calc?d for C8H7Br03 and C8H7I03, 232 and 278; found, 232 and 278. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; at 20 - 55℃; for 1.33333h; | Flaked potassium hydroxide (59.575g) was added portionwise to stirred and cooled (ice-bath) methanol (600ml_) keeping the temperature below 20C. This solution was transferred to a dropping funnel. The starting material, 4-bromo-2,6-difluoro-benzaldehyde (commercially available, Chemical Abstracts Reg. No. 537013-51 -7, 200g), was dissolved in methanol (1210ml_) at 25C. The mixture was warmed to 40C and the potassium methoxide solution added from the dropping funnel over 20 minutes with stirring. An initial exotherm was observed which was controlled by external cooling. The reaction temperature was increased to 55C and heating was continued for 1 hour. The reaction mixture was cooled to room temperature and the methanol was removed under vacuum. The resultant residue was partitioned between water (1.6L) and ethyl acetate (1 .6L). The phases were separated and the aqueous layer extracted with further ethyl acetate (2 x 0.5L). The combined organic phases were washed with water (0.5L) and concentrated under vacuum leaving a yellow solid. This solid was triturated with cold iso-hexane, filtered and dried in vacuo to give a yellow solid as a 4:1 mixture of the desired compound 4-bromo-2-fluoro-6-methoxy- benzaldehyde [1 H-NMR (400 MHz, CDCI3) 10.36 delta (delta): (s, 1 H), 6.94-6.97 (m, 2H), 3.94 (s, 3H)] and 4-bromo-2,6-dimethoxy-benzaldehyde | |
With potassium hydroxide; at 20 - 55℃; for 1.33333h; | Flaked potassium hydroxide (59.575g) was added portionwise to stirred and cooled (ice-bath) methanol (600ml_) keeping the temperature below 20C. This solution was transferred to a dropping funnel. The starting material, 4-Bromo-2,6-difluoro-benzaldehyde (commercially available, CAS 537013-51-7, 200g), was dissolved in methanol (1210ml_) at 25C. The mixture was warmed to 40C and the potassium methoxide solution added from the dropping funnel over 20 minutes with stirring. An initial exotherm was observed which was controlled by external cooling. The reaction temperature was increased to 55C and heating was continued for 1 hour. The reaction mixture was cooled to room temperature and the methanol was removed under vacuum. The resultant residue was partitioned between water (1.6L) and ethyl acetate (1 .6L). The phases were separated and the aqueous layer extracted with further ethyl acetate (2 x 0.5L). The combined organic phases were washed with water (0.5L) and concentrated under vacuum leaving a yellow solid. This solid was triturated with cold iso-hexane, filtered and dried in vacuo to give a yellow solid as a 4:1 mixture of the desired compound 4-bromo-2-fluoro-6-methoxy- benzaldehyde [1 H-NMR (400 MHz, CDCI3) 10.36 (s, 1 H), 6.94-6.97 (m, 2H), 3.94 (s, 3H)] and 4-bromo-2,6-dimethoxy-benzaldehyde. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6.834 g | With potassium hydroxide; In ethanol; | To a mixture of <strong>[1354050-38-6]4-bromo-2,6-dimethoxy-benzaldehyde</strong> (CAS 1354050-38-6, 5g) and 2,2,5,5- tetramethyltetrahydrofuran-3-one (CAS 5455-94-7, 2.90g) in ethanol (75mL) was added a solution of potassium hydroxide (0.445g) in ethanol (5m1) drop wise over 5 minutes. The mixture was stirred for 3 hours then left to stand overnight. The reaction mixture wasconcentrated, diluted with water and acidified with 2M hydrochloric acid. The suspension was extracted twice with dichloromethane. The combined organics were washed with water, brine, dried with magnesium sulfate, concentrated, triturated with ice-cold isohexane and filtered and dried to give a mixture of isomers 4-[(4-bromo-2,6-dimethoxy-phenyl)methylene]- 2,2,5,5-tetramethyl-tetrahydrofuran-3-one (6.834g) as a pale yellow solid.LC/MS 1.10mm, MH+ 369 (2mm run) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51.42% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 90℃; for 2h;Inert atmosphere; | To a stirred solution of 1 ,3-dimethyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-one (430 mg, 1 .73 mmol, 1 .0 equiv) and <strong>[1354050-38-6]4-bromo-2,6-dimethoxybenzaldehyde</strong> (634.52 mg, 2.59 mmol, 1 .50 equiv) in 1 ,4-dioxane(25 mLyPEO (5 ml_), was added Pd(dppf)Cl2 (126.3 mg, 0.17 mmol, 0.10 equiv) and CS2CO3 (1 124.78 mg, 3.45 mmol, 2.0 equiv). The resulting solution was stirred at 90 degrees C for 2 h under nitrogen atmosphere. Then the mixture was allowed to cool down to room temperature, the mixture was diluted with water (25 mL) and extracted with EtOAc (3 x 25 ml_). The organic layers were combined and dried over anhydrous sodium sulfate, filtered and concentrated to give a crude product. The residue was purified by silica gel column chromatography, eluted with ChEC /MeOH (20:1 ) to afford 4-(1 ,5- dimethyl-6-oxopyridin-3-yl)-2,6-dimethoxybenzaldehyde (313 mg, 51 .42%) as an off-white solid. LCMS (ESI) m/z: [M+H]+ = 288 |
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate; In water; N,N-dimethyl-formamide; at 100℃; for 1h;Inert atmosphere; Sealed tube; | 4-(1,5-Dimethyl-6-oxo-1,6-dihydro-pyridin-3-yl)-2,6-dimethoxy-benzaldehyde (I-205') In a vial <strong>[1354050-38-6]4-bromo-2,6-dimethoxybenzaldehyde</strong> L-100 (517.8 mg; 2.007 mmol), 1,3-dimethyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyridin-2-one J-1 (500.0 mg; 2.007 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), dichloromethane (169.0 mg; 0.201 mmol) are introduced. DMF (4 mL) and a 2N aqueous solution of sodium bicarbonate (2.5 mL) are added. The vial is flushed with argon and sealed. The reaction mixture is heated at 100 C. for 1 h. Water (a drop) is added to the reaction mixture and the mixture is filtered. The filtrate is purified with the basic (ammonia buffer) RP HPLC system (column: X-Bridge C-18 30*50 mm). The product containing fractions are concentrated under reduced pressure. HPLC/MS: (M+H)+=288; tRet=0.84 min; method M1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With titanium tetrachloride; In dichloromethane; at 0 - 20℃; for 4h; | General procedure: Anhydrous CH2Cl2 (75 mL) Dichloromethyl methyl ether (dichloromethyl methyl ether) (40 mmol) and TiCl4 (48 mmol) ofThe solution was stirred magnetically in a was treated at 0 the aryl bromide solution in dry CH2Cl2 (25 mL).The reaction mixture was stirred at room temperature for 4 hours.Followed by the addition of cold 5% HCl aqueous solution (20 mL) at 0 , stirring was continued for 15 minutes. The organic layer was then separated and the aqueous solution was extracted with CH2Cl2 (3 x 20 mL). The extract was washed with 5% aqueous NaHCO3 (80 mL) and brine (80 mL) After drying (MgSO4)Concentration under reduced pressure gave bromobenzaldehyde (compound of formula 7). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Sarcosyl tert-butyl ester hydrochloride (556 mg, 3.06 mmol, 1.5 eq) was dissolved in a solution of NaOAc (251 mg, 3.06 mmol, 1.5 eq) in DCM (8.2 mL) and 167 muL AcOH (2.04 mmol, 1.0 eq) was added followed by <strong>[1354050-38-6]4-bromo-2,6-dimethoxybenzaldehyde</strong> (500 mg, 2.04 mmol, 1.0 eq). The mixture was stirred for 10 minutes before sodium triacetoxy borohydride was added in one portion (864.8 mg, 4.08 mmol, 2.0 eq) and the mixture was stirred for 18 hours. The reaction was basified to approximately pH 11 with 1M K2CO3and extracted 4 times with DCM (10 mL). The combined organics were washed with deionized water (10 mL) and saturated brine (10 mL) before being dried over Na2SO4and concentrated in vacuo to afford the desired product as an off-white solid (725 mg, 95%). | |
65.09% | To a stirred solution of tert-butyl 2-(methylamino)acetate hydrochloride (5.93 g, 32.643 mmol, 1 .60 equiv) in MeOH (60 ml_) was added <strong>[1354050-38-6]4-bromo-2,6-dimethoxybenzaldehyde</strong> (5 g, 20.402 mmol, 1 equiv), and the mixture was stirred for 30 minutes before NaBEhCN (2.56 g, 40.737 mmol, 2.00 equiv) was added in portions. The resulting solution was stirred for another 3 hours at 25 degrees C. Then the mixture was concentrated. The residue was purified by silica gel column chromatography, eluted with EA/PE (1 :1 ) to afford ferf-butyl 2-[[(4-bromo-2,6-dimethoxyphenyl)methyl] (methyl)amino]acetate (4.97 g, 65.09%) as a white solid. LCMS (ESI) m/z: [M+H]+ = 374 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With bis(tri-t-butylphosphine)palladium(0); triethylamine; In toluene; at 80℃; for 16h;Inert atmosphere; | 2,6-Dimethoxy-4-bromobenzaldehyde (570mg, 2.34mmol) and vinylboronic acid pinacol ester (504mg, 3.27mmol) were dissolved in toluene (10mL), followed by addition of bis(tri-tert-butylphosphine)palladium (200mg, 0.4mmol) and triethylamine (1.9g, 18.72mmol). After the reaction system was purged three times with nitrogen, the reaction solution was heated to 80C and stirred for 16 hours. Then the reaction solution was cooled to room temperature and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 3:1) to give compound 64-b as a pale brown solid (540mg, yield 73%). 1H-NMR (500MHz, DMSO-d6) delta: 10.32 (s, 1H), 7.31 (d, J=18Hz, 1H), 6.96 (s, 2H), 6.42 (d, J=18Hz, 1H), 3.86 (s, 6H), 1.26 (s, 12H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With copper(I) oxide; caesium carbonate; In N,N-dimethyl-formamide; at 85℃; for 16h; | Compound 60-c (192mg, 1.0mmol) and <strong>[1354050-38-6]4-bromo-2,6-dimethoxybenzaldehyde</strong> (171.5mg, 0.7mmol) were dissolved in N,N-dimethylformamide (6mL), then cuprous oxide (14.4mg, 0.1mmol) and cesium carbonate (455mg, 1.4mmol) were successively added. The reaction solution was heated to 85C and stirred for 16 hours, then diluted with water (40mL), extracted with ethyl acetate (50mL x 3). The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 5:1) to give compound 60-b as a yellow solid (106mg, yield 29%). LC-MS (ESI): m/z = 357 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃; for 12h;Inert atmosphere; | Under the protection of argon, palladium acetate (0.2 mmol), binaphthyl diphenyl phosphate (0.3 mmol), cesium carbonate (24 mmol) and <strong>[1354050-38-6]4-bromo-2,6-dimethoxybenzaldehyde</strong> (2.45) were added to the three-necked flask. g, 10 mmol).Further, toluene and benzophenone imine (20 mL) were added to the reaction system, and the mixture was reacted at 100 C for 12 hours while stirring with a magnetic stirrer. After the reaction is completed, the organic phase is spin-dried, and the crude product is subjected to a silica gel column using a developing solvent ethyl acetate/petroleum ether.Obtained as a pale yellow solid (2.42 g, 70%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72.94% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 90℃; for 3h; | To a solution of <strong>[1354050-38-6]4-bromo-2,6-dimethoxybenzaldehyde</strong> (4.00 g, 16.322 mmol, 1 .00 equiv) and KOAc (4.81 g, 48.965 mmol, 3.00 equiv) in 1 ,4-dioxane(30.00 ml) was added Bis(pinacolato)diboron (4.97 g, 19.586 mmol, 1 .20 equiv) and Pd(dppf)Cl2 CH2CI2 (1 .33 g, 1 .632 mmol, 0.10 equiv). The resulting solution was stirred for 3 hours at 90 C. The solids were filtered out. The resulting mixture was concentrated. This resulted in 2.5 g (72.94%) of (4-formyl-3,5 -dimethoxyphenyl)boronic acid as a brown solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 25 - 80℃; for 1h;Inert atmosphere; | To a solution of <strong>[1354050-38-6]4-bromo-2,6-dimethoxybenzaldehyde</strong> (5.00 g, 20.402 mmol, 1 equiv) in 1 ,4- dioxane (300 ml_) was added 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl) -1 ,3,2- dioxaborolane (6.22 g, 24.483 mmol, 1 .2 equiv), Pd(dppf)Cl2 (298.57 mg, 0.408 mmol, 0.02 equiv), and KOAc (4.00 g, 40.804 mmol, 2 equiv) at 25 C. The resulting mixture was stirred at 80 C for 1 hour under N2 atmosphere. The mixture was cooled to 60 C. Then 4-bromo-2-methyl-1 ,2-dihydro-2,7- naphthyridin-1 -one (4.91 g, 20.538 mmol, 1 equiv), CS2CO3 (13.38 g, 41 .076 mmol, 2 equiv), Pd(dppf)Cl2 (298.57 mg, 0.408 mmol, 0.02 equiv), and water (60 ml_) were added. The resulting mixture was stirred at 80 O for 1 hour. The mixture was filtered and activated charcoal (5 g) was added to the filtrate and refluxed at 100 C for 1 hour. The mixture was filtered and concentrated to get crude product, which was slurried in EA, EtOH, and water respectively to afford light brown solid. This solid was dissolved in DCM and MeOH (200 ml_, v/v=20/1 ), and then precipitated with EA (200 ml_) dropwise under stirring. The solid was filtered and dried to afford 2,6-dimethoxy-4-(2-methyl-1 -oxo-1 ,2-dihydro-2,7-naphthyridin-4- yl)benzaldehyde (2.3 g, 34.63%) as light grey solid. LCMS (ESI, m/z) [M+H]+ = 325.2. 1H NMR (300 MHz, DMSO) d 10.41 (s, 1 H), 9.46 (s, 1 H), 8.74 (d, J = 5.7 Hz, 1 H), 7.99 (s, 1 H), 7.64 (d, J = 5.7Hz, 1 H), 6.85 (s, 2H), 3.89 (s, 6H), 3.62 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55.55% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 90℃; for 2h;Inert atmosphere; | To the solution of 2-methyl-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 ,2-dihydro-2,7- naphthyridin-1 -one (1 .62 g, 5.662 mmol, 1 equiv) in dioxane (30 ml_) was added 4-bromo-2,6- dimethoxybenzaldehyde (1 .39 g, 5.662 mmol, 1 equiv), Pd(dppf)Cl2 (414.26 mg, 0.566 mmol, 0.1 equiv), CS2CO3 (5.53 g, 1 6.985 mmol, 3 equiv), and H2O (3 ml_). The resulting solution was stirred at 90 C for 2 hours under nitrogen atmosphere. The resulting solution was concentrated. The residue was purified by Flash column chromatography with EtOAc/PE (0-100%) to give compound 2,6-dimethoxy-4-(2-methyl-1 - oxo-1 ,2-dihydro-2,7-naphthyridin-4-yl)benzaldehyde (1 .02 g, 55.55%) as yellow solid. LCMS (ESI) m/z: [M+H]+ = 325. |
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