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CAS No. : | 694-85-9 | MDL No. : | MFCD00006520 |
Formula : | C6H7NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DVVGIUUJYPYENY-UHFFFAOYSA-N |
M.W : | 109.13 | Pubchem ID : | 12755 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 31.96 |
TPSA : | 22.0 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.13 cm/s |
Log Po/w (iLOGP) : | 1.56 |
Log Po/w (XLOGP3) : | -0.23 |
Log Po/w (WLOGP) : | 0.39 |
Log Po/w (MLOGP) : | 0.59 |
Log Po/w (SILICOS-IT) : | 0.96 |
Consensus Log Po/w : | 0.65 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.93 |
Solubility : | 12.9 mg/ml ; 0.118 mol/l |
Class : | Very soluble |
Log S (Ali) : | 0.23 |
Solubility : | 183.0 mg/ml ; 1.68 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -1.43 |
Solubility : | 4.06 mg/ml ; 0.0372 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.15 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
38% | Stage #1: With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuranSchlenk technique; Inert atmosphere; Reflux Stage #2: With copper(ll) bromide In methanol; water at 80℃; for 18 h; |
General procedure: A Schlenk tube was charged with the 2-pyridone substrate (1.0 mmol) [in the case of a liquid substrate, this was added neat after the solvent], [Ir(cod)(OMe)]2 (6.6 mg, 0.01 equiv), 4,4′-di-tert-butyl-2,2′-dipyridyl (5.4 mg, 0.02 equiv) and bis(pinacolato)diboron (178 mg, 0.70 equiv). After purging with nitrogen, deoxygenated and anhydrous THF (1.4 mL) was added and the reaction mixture was heated at reflux for 48 h (in cases where full conversion occurred after 24 h, the reaction was halted at that time). The volatile materials were then removed under reduced pressure and the crude product was dissolved in MeOH (2.5 mL) and a solution of CuBr2 (670 mg, 3.0 mmol) in H2O (2.5 mL) was added. The reaction mixture was heated at 80 °C for 18 h under air, cooled to r.t., diluted with NH4OH (5 mL, 15percent aq) and extracted with CH2Cl2 (5 × 5 mL). The combined extracts were dried (MgSO4), filtered and concentrated in vacuo. Purification of the crude reaction mixture by flash column chromatography on silica gel afforded the desired product. Table 1 shows the product distributions of 2–5 but no attempt was made to optimise monosubstitution (vs. disubstitution) in the case of 1b or 1c. According to General Procedure 1, analysis of the 1H NMR spectrum ofthe crude reaction mixture showed a conversion of 100percent. Products 5-bromo-1-methylpyridin-2(1H)-one (3b), 4-bromo-1-methylpyridin-2(1H)-one (2b), 4,6-dibromo-1- methylpyridin-2(1H)-one (4b) and 3,5-dibromo-1-methylpyridin-2(1H)-one (5b) were generated in a 35:5:39:21 ratio. Purification by flash column chromatography on silica gel (n-hexane–EtOAc, 70:30 to EtOAc, 100percent) gave an inseparable 95:5 mixture of 5-bromo-1-methylpyridin-2(1H)-one (3b) and 4-bromo-1-methylpyridin-2(1H)-one (2b) (71 mg, 38percent) as an orange oil. 2b (minor component) Rf = 0.24 (EtOAc). 1H NMR (400 MHz, CDCl3): δ = 7.11 (d, J = 7.5 Hz, 1 H), 6.79 (d,J = 2.0 Hz, 1 H), 6.28 (dd, J = 2.0, 7.5 Hz, 1 H), 3.50 (s, 3 H). The spectroscopic properties of this compound were consistent with data available in literature. 3b (major component) Rf = 0.24 (EtOAc).1H NMR (400 MHz, CDCl3): δ = 7.39 (d, J = 2.5 Hz, 1 H), 7.33 (dd,J = 2.5, 9.5 Hz, 1 H), 6.46 (d, J = 9.5 Hz, 1 H), 3.50 (s, 3 H). The spectroscopic properties of this compound were consistent with data availablein literature.19a4,6-Dibromo-1-methylpyridin-2(1H)-one (4b) Yield: 58 mg (22percent); off-white solid; Rf = 0.59 (EtOAc). IR (neat): 3111, 2922, 2851, 1650, 1566, 1495 cm–1. 1H NMR (400 MHz, CDCl3): δ = 6.75 (s, 1 H), 6.66 (s, 1 H), 3.68 (s, 3 H).13C NMR (100 MHz, CDCl3): δ = 161.5, 134.8, 128.3, 120.7, 114.4, 36.4.HRMS-ESI: m/z [M + H]+ calcd for C6H679Br2NO: 265.8811; found:265.8799.3,5-Dibromo-1-methylpyridin-2(1H)-one (5b)Yield: 28 mg (11percent); white solid; Rf = 0.51 (EtOAc). 1H NMR (400 MHz, CDCl3): δ = 7.77 (d, J = 2.0 Hz, 1 H), 7.43 (d,J = 2.0 Hz, 1 H), 3.58 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 158.0, 143.8, 137.5, 117.4, 96.5, 39.0. The spectroscopic properties of this compound were consistent withthe data available in literature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.2 g | With bromine In chloroform at 20℃; Reflux | A solution of bromine (2.3 mL, 46 mmol) and chloroform (10 mL) was added to a stirring solution of l-methyl-2-pyridone (5.0 mL, 456 mmol) and chloroform (46 mL) at reflux. After 1 h, the reaction mixture was cooled to room temperature. After 72 h, the reaction mixture was filtered and the filter cake was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The layers were separated, silica gel (1.0 g) was added to the organic material, and the volatiles were removed under a vacuum. The residue was subjected to flash chromatography on silica gel (120 g RediSep® normal phase column, gradient elution of 0 to 100percent ethyl acetate-hexane, Teledyne Isco, Lincoln, NE) to afford 5-bromo-l-methylpyridin-2(lH)-one (1.2 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | Stage #1: With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuranSchlenk technique; Inert atmosphere; Reflux Stage #2: With copper(ll) bromide In methanol; water at 80℃; for 18 h; |
General procedure: A Schlenk tube was charged with the 2-pyridone substrate (1.0 mmol) [in the case of a liquid substrate, this was added neat after the solvent], [Ir(cod)(OMe)]2 (6.6 mg, 0.01 equiv), 4,4′-di-tert-butyl-2,2′-dipyridyl (5.4 mg, 0.02 equiv) and bis(pinacolato)diboron (178 mg, 0.70 equiv). After purging with nitrogen, deoxygenated and anhydrous THF (1.4 mL) was added and the reaction mixture was heated at reflux for 48 h (in cases where full conversion occurred after 24 h, the reaction was halted at that time). The volatile materials were then removed under reduced pressure and the crude product was dissolved in MeOH (2.5 mL) and a solution of CuBr2 (670 mg, 3.0 mmol) in H2O (2.5 mL) was added. The reaction mixture was heated at 80 °C for 18 h under air, cooled to r.t., diluted with NH4OH (5 mL, 15percent aq) and extracted with CH2Cl2 (5 × 5 mL). The combined extracts were dried (MgSO4), filtered and concentrated in vacuo. Purification of the crude reaction mixture by flash column chromatography on silica gel afforded the desired product. Table 1 shows the product distributions of 2–5 but no attempt was made to optimise monosubstitution (vs. disubstitution) in the case of 1b or 1c. According to General Procedure 1, analysis of the 1H NMR spectrum ofthe crude reaction mixture showed a conversion of 100percent. Products 5-bromo-1-methylpyridin-2(1H)-one (3b), 4-bromo-1-methylpyridin-2(1H)-one (2b), 4,6-dibromo-1- methylpyridin-2(1H)-one (4b) and 3,5-dibromo-1-methylpyridin-2(1H)-one (5b) were generated in a 35:5:39:21 ratio. Purification by flash column chromatography on silica gel (n-hexane–EtOAc, 70:30 to EtOAc, 100percent) gave an inseparable 95:5 mixture of 5-bromo-1-methylpyridin-2(1H)-one (3b) and 4-bromo-1-methylpyridin-2(1H)-one (2b) (71 mg, 38percent) as an orange oil. 2b (minor component) Rf = 0.24 (EtOAc). 1H NMR (400 MHz, CDCl3): δ = 7.11 (d, J = 7.5 Hz, 1 H), 6.79 (d,J = 2.0 Hz, 1 H), 6.28 (dd, J = 2.0, 7.5 Hz, 1 H), 3.50 (s, 3 H). The spectroscopic properties of this compound were consistent with data available in literature. 3b (major component) Rf = 0.24 (EtOAc).1H NMR (400 MHz, CDCl3): δ = 7.39 (d, J = 2.5 Hz, 1 H), 7.33 (dd,J = 2.5, 9.5 Hz, 1 H), 6.46 (d, J = 9.5 Hz, 1 H), 3.50 (s, 3 H). The spectroscopic properties of this compound were consistent with data availablein literature.19a4,6-Dibromo-1-methylpyridin-2(1H)-one (4b) Yield: 58 mg (22percent); off-white solid; Rf = 0.59 (EtOAc). IR (neat): 3111, 2922, 2851, 1650, 1566, 1495 cm–1. 1H NMR (400 MHz, CDCl3): δ = 6.75 (s, 1 H), 6.66 (s, 1 H), 3.68 (s, 3 H).13C NMR (100 MHz, CDCl3): δ = 161.5, 134.8, 128.3, 120.7, 114.4, 36.4.HRMS-ESI: m/z [M + H]+ calcd for C6H679Br2NO: 265.8811; found:265.8799.3,5-Dibromo-1-methylpyridin-2(1H)-one (5b)Yield: 28 mg (11percent); white solid; Rf = 0.51 (EtOAc). 1H NMR (400 MHz, CDCl3): δ = 7.77 (d, J = 2.0 Hz, 1 H), 7.43 (d,J = 2.0 Hz, 1 H), 3.58 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 158.0, 143.8, 137.5, 117.4, 96.5, 39.0. The spectroscopic properties of this compound were consistent withthe data available in literature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | at 100℃; | To a stirred mixture of 1-METHYL-LH-PYRIDIN-2-ONE (33.47 g, 0.306 mol) and concentrated H2S04 (300 ML) at 100 °C was added concentrated HNO3 (120 mL) in portions. The reaction mixture was heated at this temperature overnight, and then poured into ice (1400 mL). The precipitate was filtered off and washed with water to give the title compound (Yield: 18.66 g, 30percent). LH NMR (400 MHZ, CDCl3) : 8 9.05 (d, 1H), 8.90 (d, 1H), 3.80 (s, 3H). |
28% | at 0 - 100℃; for 5 h; | 1-Methyl-2-pyridone (25.0 g, 0.229 mol) was added to sulfuric acid (500 mL) at 0° C. After stirring for 5 min., nitric acid (200 mL) was added dropwise at 0° C. After addition, the reaction temperature was slowly raised to 100° C., and then maintained for 5 h. The reaction mixture was poured into ice, basified with potassium carbonate to pH 8 and extracted with CH2Cl2 (100 mL*3). The combined organic layers were dried over Na2SO4 and concentrated to yield 1-methyl-3,5-dinitro-2-pyridone (12.5 g, 28percent), which was used without further purification. |
22% | at 100℃; for 4 h; | Step 1: To a solution of N-methylpyridinone (A) (3 g, 27.49 mmol) in H2SO4 (100 mL) was slowly added HNO3 (60 percent) (0.3 mL, 137.45 mmol) at room temperature. The reaction mixture was heated to 100 °C for 4 h. TLC showed complete consumption of starting material. The reaction mixture was cooled to room temperature and neutralized with NaHCO3. The mixture was extracted with ethyl acetate and washed with water and brine. The extract was dried over MgSO4 and concentrated under reduced pressure to give 1-methyl-3,5-dinitropyridin-2(1H)-one (B) (1.19 g, 22 percent) |
22% | at 20 - 100℃; | To a solution of N-methylpyridinone (A) (3 g, 27.49 mmol) in H2SO4 (100 mL) was slowly added HNO3 (60percent) (0.3 mL, 137.45 mmol) at room temperature. The reaction mixture was heated to 100° C. for 4 h. TLC showed complete consumption of starting material. The reaction mixture was cooled to room temperature and neutralized with NaHCO3. The mixture was extracted with ethyl acetate and washed with water and brine. The extract was dried over MgSO4 and concentrated under reduced pressure to give 1-methyl-3,5-dinitropyridin-2(1H)-one (B) (1.19 g, 22percent) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | Stage #1: With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuranSchlenk technique; Inert atmosphere; Reflux Stage #2: With copper(ll) bromide In methanol; water at 80℃; for 18 h; |
General procedure: A Schlenk tube was charged with the 2-pyridone substrate (1.0 mmol) [in the case of a liquid substrate, this was added neat after the solvent], [Ir(cod)(OMe)]2 (6.6 mg, 0.01 equiv), 4,4′-di-tert-butyl-2,2′-dipyridyl (5.4 mg, 0.02 equiv) and bis(pinacolato)diboron (178 mg, 0.70 equiv). After purging with nitrogen, deoxygenated and anhydrous THF (1.4 mL) was added and the reaction mixture was heated at reflux for 48 h (in cases where full conversion occurred after 24 h, the reaction was halted at that time). The volatile materials were then removed under reduced pressure and the crude product was dissolved in MeOH (2.5 mL) and a solution of CuBr2 (670 mg, 3.0 mmol) in H2O (2.5 mL) was added. The reaction mixture was heated at 80 °C for 18 h under air, cooled to r.t., diluted with NH4OH (5 mL, 15percent aq) and extracted with CH2Cl2 (5 × 5 mL). The combined extracts were dried (MgSO4), filtered and concentrated in vacuo. Purification of the crude reaction mixture by flash column chromatography on silica gel afforded the desired product. Table 1 shows the product distributions of 2–5 but no attempt was made to optimise monosubstitution (vs. disubstitution) in the case of 1b or 1c. According to General Procedure 1, analysis of the 1H NMR spectrum ofthe crude reaction mixture showed a conversion of 100percent. Products 5-bromo-1-methylpyridin-2(1H)-one (3b), 4-bromo-1-methylpyridin-2(1H)-one (2b), 4,6-dibromo-1- methylpyridin-2(1H)-one (4b) and 3,5-dibromo-1-methylpyridin-2(1H)-one (5b) were generated in a 35:5:39:21 ratio. Purification by flash column chromatography on silica gel (n-hexane–EtOAc, 70:30 to EtOAc, 100percent) gave an inseparable 95:5 mixture of 5-bromo-1-methylpyridin-2(1H)-one (3b) and 4-bromo-1-methylpyridin-2(1H)-one (2b) (71 mg, 38percent) as an orange oil. 2b (minor component) Rf = 0.24 (EtOAc). 1H NMR (400 MHz, CDCl3): δ = 7.11 (d, J = 7.5 Hz, 1 H), 6.79 (d,J = 2.0 Hz, 1 H), 6.28 (dd, J = 2.0, 7.5 Hz, 1 H), 3.50 (s, 3 H). The spectroscopic properties of this compound were consistent with data available in literature. 3b (major component) Rf = 0.24 (EtOAc).1H NMR (400 MHz, CDCl3): δ = 7.39 (d, J = 2.5 Hz, 1 H), 7.33 (dd,J = 2.5, 9.5 Hz, 1 H), 6.46 (d, J = 9.5 Hz, 1 H), 3.50 (s, 3 H). The spectroscopic properties of this compound were consistent with data availablein literature.19a4,6-Dibromo-1-methylpyridin-2(1H)-one (4b) Yield: 58 mg (22percent); off-white solid; Rf = 0.59 (EtOAc). IR (neat): 3111, 2922, 2851, 1650, 1566, 1495 cm–1. 1H NMR (400 MHz, CDCl3): δ = 6.75 (s, 1 H), 6.66 (s, 1 H), 3.68 (s, 3 H).13C NMR (100 MHz, CDCl3): δ = 161.5, 134.8, 128.3, 120.7, 114.4, 36.4.HRMS-ESI: m/z [M + H]+ calcd for C6H679Br2NO: 265.8811; found:265.8799.3,5-Dibromo-1-methylpyridin-2(1H)-one (5b)Yield: 28 mg (11percent); white solid; Rf = 0.51 (EtOAc). 1H NMR (400 MHz, CDCl3): δ = 7.77 (d, J = 2.0 Hz, 1 H), 7.43 (d,J = 2.0 Hz, 1 H), 3.58 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 158.0, 143.8, 137.5, 117.4, 96.5, 39.0. The spectroscopic properties of this compound were consistent withthe data available in literature. |
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