Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 337463-88-4 | MDL No. : | MFCD11101028 |
Formula : | C7H5BrN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GDVHYNCHZKTTSQ-UHFFFAOYSA-N |
M.W : | 229.03 | Pubchem ID : | 21873772 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 48.76 |
TPSA : | 51.22 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) : | -6.87 cm/s |
Log Po/w (iLOGP) : | 1.69 |
Log Po/w (XLOGP3) : | 1.16 |
Log Po/w (WLOGP) : | 0.6 |
Log Po/w (MLOGP) : | 0.51 |
Log Po/w (SILICOS-IT) : | 1.7 |
Consensus Log Po/w : | 1.13 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.36 |
Solubility : | 0.998 mg/ml ; 0.00436 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.83 |
Solubility : | 3.38 mg/ml ; 0.0148 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.12 |
Solubility : | 0.175 mg/ml ; 0.000766 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.36 |
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: |
* 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 |
---|---|---|
95% | at 100℃; for 2 h; | Compound 3.1 (2.7 g, 8.85 mmol) And iron powder (2.48g, 44.3mmol) Add to acetic acid (40 mL), The reaction system was stirred at 100 ° C for 2 hours. Cool to room temperature, The reaction solution was filtered through celite. Add water (100 mL) to the filtrate. Extracted with dichloromethane (20 mL x 3), Combine the organic phase, Drying with anhydrous sodium sulfate, concentrate, The residue was subjected to silica gel column chromatography ( petroleum ether / ethyl acetate = 3/1) Purification of compound 3.2 (1.9 g, yield: 95percent) It is a pale yellow liquid. |
80% | at 80℃; | Compound 1a was synthesized from 5 using same procedure as mentioned for compound 1c in 80percent yield. 1H NMR (300 MHz, DMSO-d6) δ = 4.66 (s, 2 H) 7.16 (d, J=8.29 Hz, 1 H) 7.32 (d, J=8.29 Hz, 1 H) 11.50 (s, 1 H); 13C NMR (300 MHz, DMSO-d6) δ = 66.61 , 121.99 , 126.08 , 129.63 , 138.83 , 142.04 , 165.48; HRMS m/z (EI) calcd. for C7H5BrN2O2 227.9534, found 228.9694 [M+H]+ |
76% | Stage #1: at 100℃; for 2 h; Stage #2: With sodium hydrogencarbonate In water; ethyl acetate |
Step 3 To a solution of Compound (8) (5.50 g, 18.0 mmol) in acetic acid (60 mL), iron powder (10.1 g, 180 mmol) was added. The solution was then stirred at 100°C for 2 hours. The reaction solution was filtered through a Celite pad, and then the filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with aqueous saturated sodium bicarbonate, dried with anhydrous magnesium sulfate, and then concentrated in vacuo. The resulting powder was further washed with ethyl acetate and hexane to yield the subject compound (9) (3.12 g, 76percent) as a white powder.1H-NMR (DMSO-d6) δ11.48 (1H, s), 7.31 (1H, d, J = 8.1 Hz), 7.16 (1H, d, J = 8.1 Hz), 4.66 (2H, s). |
76.28% | at 100℃; for 6 h; | To a stirred solution of ethyl 2-((6-bromo-2-nitropyridin-3-yl)oxy)acetate, lb (21g, 0.0687mol) in glacial acetic acid (400ml), Iron powder(l 1.51g, 0.2063mol) was added and heated to 100°C for 6 hours. After completion of the reaction, reaction mixture was filtered through celite bed using ethyl acetate, 10percent Methanol and concentrated in vacuo. It was washed with Methanol to obtain pure 6-bromo-2H-pyrido[3,2-b][l,4]oxazin- 3(4H)-one, I (12g, 76.28percent ). LCMS = Calculated for C7H5BrN202, 229.03, Observed = 230.2. |
57% | at 90℃; for 6 h; | C. 6-Bromo-4H-pyrido[3,2-b][1,4]oxazin-3-one. To a solution of (6-bromo-2-nitro-pyridin-3-yloxy)-acetic acid ethyl ester (3.14 g, 10.3 mmol) in glacial acetic acid (12.4 mL) was added iron powder (1.67 g, 29.9 mmol). The suspension was heated to 90° C. and stirred for 6 h, after which it was cooled to RT and diluted with EtOAc (50 mL). The mixture was filtered through a pad of SiO2 and the filtrate was concentrated. Recrystallization from CH3OH provided 1.32 g (57percent) of the title compound as a solid. MS (ESI): exact mass calculated for C7H5BrN2O2, 227.95; m/z found, 228.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.98 (d, J=5.3, 1H), 7.16-7.09 (m, 1H), 6.98 (dd, J=8.0, 4.9, 1H), 4.68 (d, J=1.4, 2H). |
52% | at 90℃; for 5 h; | c) 6-Bromo-4H-pyrido[3,2-b][1 ,4]oxazin-3-one; Ethyl (6-bromo-2-nitro-pyridin-3-yloxy)acetate (38 g, 0.125 mole) was dissolved in glacial AcOH (150 mL), and iron powder (20 g, 0.36 mole) was added. The mixture was mechanically stirred and heated at 90 0C for 5 hr, then was cooled to room temperature and diluted with EtOAc (300 mL). The mixture was filtered through a pad of silica gel and the filtrate was concentrated in vacuo and the residue recrystallized from MeOH (15 g,52percent); MS (ES) m/z 229.0 (M + H)+. |
52% | at 90℃; for 5 h; | (c) 6-Bromo-4f/-pyrido[3,2-b][1 ,4]oxazin-3-one; Ethyl (6-bromo-2-nitro-pyridin-3-yloxy)acetate (38 g, 0.125 mole) was dissolved in glacial AcOH (150 ml_), and iron powder (20 g, 0.36 mole) was added. The mixture was mechanically stirred and heated at 90 0C for 5 hr, then was cooled to room temperature and diluted with EtOAc (300 ml_). The mixture was filtered through a pad of silica gel and the filtrate was concentrated in vacuo and the residue recrystallized from MeOH (15 g, 52percent): MS (ES) m/z 229.0 (M + H)+. |
52% | at 90℃; for 5 h; | Ethyl (6-bromo-2-nitro-pyridin-3-yloxy)acetate (38 g, 0.125 mole) was dissolved in glacial AcOH (150 mL), and iron powder (20 g, 0.36 mole) was added. The mixture was mechanically stirred and heated at 90 0C for 5 hr, then was cooled to room temperature and diluted with EtOAc (300 mL). The mixture was filtered through a pad of silica gel and EPO <DP n="24"/>the filtrate was concentrated in vacuo and the residue recrystallized from MeOH (15 g, 52percent); MS (ES) m/z 229.0 (M + H)+. |
52% | With iron In acetic acid at 90℃; for 5 h; | Ethyl (6-bromo-2-nitro-pyridin-3-yloxy)acetate (38 g, 0.125 mole) was dissolved in glacial AcOH (150 mL), and iron powder (20 g, 0.36 mole) was added. The mixture was mechanically stirred and heated at 90 0C for 5 hr, then was cooled to room temperature and diluted with EtOAc (300 mL). The mixture was filtered through a pad of silica gel and EPO <DP n="24"/>the filtrate was concentrated in vacuo and the residue recrystallized from MeOH (15 g, 52percent): MS (ES) m/z 229.0 (M + H)+. |
52% | With iron In acetic acid at 90℃; for 5 h; | Ethyl (6-bromo-2-nitro-pyridin-3-yloxy)acetate (38 g, 0.125 mole) was dissolved in glacial AcOH (150 mL), and iron powder (20 g, 0.36 mole) was added. The mixture was mechanically stirred and heated at 90 0C for 5 h,,then was cooled to room temperature and diluted with EtOAc (300 mL). The mixture was filtered through a pad of silica gel and the filtrate was concentrated in vacuo and the residue recrystallized from MeOH (15 g, 52percent); MS (ES) m/z229.0 (M + H)+. |
52% | at 90℃; for 5 h; | c) 6-Bromo-4H-pyrido[3,2-b][1,4]oxazin-3-one; Ethyl (6-bromo-2-nitro-pyridin-3-yloxy)acetate (38 g, 0.125 mole) was dissolved in glacial AcOH (150 mL), and iron powder (20 g, 0.36 mole) was added. The mixture was mechanically stirred and heated at 90° C. for 5 hr, then was cooled to room temperature and diluted with EtOAc (300 mL). The mixture was filtered through a pad of silica gel and the filtrate was concentrated in vacuo and the residue recrystallized from MeOH (15 g, 52percent); MS (ES) m/z229.0 (M+H)+.; c) 6-Bromo-4H-Pyrido[3,2-b][1,4]oxazin-3-one; The nitropyridine (38 g, 0.125 mole) was dissolved in glacial AcOH (150 mL), and iron powder (20 g, 0.36 mole) was added. The mixture was mechanically stirred and heated at 90° C. for 5 hr, then was cooled to room temperature and diluted with EtOAc (300 mL). The mixture was filtered through a pad of silica gel and the filtrate was concentrated in vacuo and the residue recrystallized from MeOH (15 g, 52percent). MS (ES) m/z 229.0 (M+H)30 . |
52% | at 90℃; for 5 h; | The nitropyridine (g) (38 g, 0.125 mol) was dissolved in glacial AcOH (150 ml), and iron powder (20 g, 0.36 mole) was added. The mixture was mechanically stirred and heated at 90°C for 5 hours, then was cooled to room temperature and diluted with EtOAc (300 ml). The mixture was filtered through a pad of silica gel and the filtrate was concentrated ira vacuo and the residue recrystallized from MeOH (15 g, 52percent). MS (+ve ion electrospray) m/z 229 (MH+). |
52% | With iron In acetic acid at 90℃; for 5 h; | The nitropyridine (g) (38 g, 0.125 mole) was dissolved in glacial [ACOH] (150 mL), and iron powder (20 g, 0.36 mole) was added. The mixture was mechanically stirred and heated at [90 °C] for 5 hr, then was cooled to room temperature and diluted with EtOAc (300 mL). The mixture was filtered through a pad of silica gel and the filtrate was concentrated [IN VACUO] and the residue recrystallized from MeOH (15 g, 52percent). MS (ES) [M/Z] 229.0 (M + H) +. |
52% | at 90℃; for 5 h; | Ethyl ester (3b) (38 g, 0.125 mol) was dissolved in glacial AcOH (150 mL), and iron powder (20 g, 0.36 mol) was added. The mixture was mechanically stirred and heated at 90 degree;C for 5 h, then was cooled to room temperature and diluted with EtOAc (300 mL). The mixture was filtered through a pad of silica gel and the filtrate was concentrated in vacuo and the residue recrystallized from MeOH (15 g, 52percent). MS (ES) m/z 229.0 (M + H)+ |
52% | at 90℃; for 5 h; | The nitropyridine (305b) (38 g, 0.125 mole) was dissolved in glacial AcOH (150 ml), and iron powder (20 g, 0.36 mole) was added. The mixture was mechanically stirred and heated at 90 °C for 5 hr, then was cooled to room temperature and diluted with EtOAc (300 ml). The mixture was filtered through a pad of silica gel and the filtrate was concentrated in vacuo and the residue recrystallized from MeOH (15 g, 52percent). MS (ES) m/z 229.0 (M + H) +. |
52% | at 90℃; for 5 h; | c) 6-Bromo-4/-/-pyrido[3,2-b][1 ,4]oxazin-3-one; Ethyl (6-bromo-2-nitro-pyridin-3-yloxy)acetate (38 g, 0.125 mole) was dissolved in glacial AcOH (150 ml_), and iron powder (20 g, 0.36 mole) was added. The mixture was mechanically stirred and heated at 90 °C for 5 hr, then was cooled to room temperature and diluted with EtOAc (300 mL). The mixture was filtered through a pad of silica gel and the filtrate was concentrated in vacuo and the residue recrystallized from MeOH (15 g, 52percent); MS (ES) m/z 229.0 (M + H)+. |
52% | at 90℃; for 5 h; | c) 6-Bromo-4H-pyrido[3,2-b][1,4]oxazin-3-one; Ethyl (6-bromo-2-nitro-pyridin-3-yloxy)acetate (38 g, 0.125 mole) was dissolved inglacial AcOH (150 mL), and iron powder (20 g, 0.36 mole) was added. The mixture wasmechanically stirred and heated at 90 °C for 5 hr, then was cooled to room temperatureand diluted with EtOAc (300 mL). The mixture was filtered through a pad of silica gel andthe filtrate was concentrated in vacua and the residue recrystallized from MeOH (15 g,52percent); MS (ES) m/z 229.0 (M + H)+.; c) 6-Bromo-4/-/-pyrido[3,2-b][1,4]oxazin-3-one; The nitropyridine (38 g, 0.125 mole) was dissolved in glacial AcOH (150 mL), andiron powder (20 g, 0.36 mole) was added. The mixture was mechanically stirred andheated at 90 °C for 5 hr, then was cooled to room temperature and diluted with EtOAcrni . i ne mixiure was mieitiu through a pad of silica gel and the filtrate wasconcentrated in vacua and the residue recrystallized from MeOH (15 g, 52percent).MS (ES) m/z229.0 (M + H)+. |
52% | at 90℃; for 5 h; | (c) 6-Bromo-4/-/-pyrido[3,2-b][1,4]oxazin-3-one; Ethyl (6-bromo-2-nitro-pyridin-3-yloxy)acetate (38 g, 0.125 mole) was dissolved in glacial AcOH (150 mL), and iron powder (20 g, 0.36 mole) was added. The mixture was mechanically stirred and heated at 90 °C for 5 h, then was cooled to room temperature and diluted with EtOAc (300 mL). The mixture was filtered through a pad of silica gel and the filtrate was concentrated in vacuo and the residue recrystallized from MeOH (15 g, 52percent); MS (ES) m/z 229.0 (M + H)+. |
52% | at 90℃; for 5 h; | c) 6-Bromo-4H-pyrido[3,2-b][1 ,4]oxazin-3-one Ethyl (6-bromo-2-nitro-pyridin-3-yloxy)acetate (38 g, 0.125 mole) was dissolved in glacial AcOH (150 ml_), and iron powder (20 g, 0.36 mole) was added. The mixture was mechanically stirred and heated at 90 0C for 5 hr, then was cooled to room temperature and diluted with EtOAc (300 ml_). The mixture was filtered through a pad of silica gel and the filtrate was concentrated in vacuo and the residue recrystallized from MeOH (15 g, 52percent); MS (ES) m/z 229.0 (M + H)+. |
52% | at 90℃; for 5 h; | Ethyl (6-bromo-2-nitro-pyridin-3-yloxy)acetate (38 g, 0.125 mole) was dissolved in glacial AcOH (150 mL), and iron powder (20 g, 0.36 mole) was added. The mixture was mechanically stirred and heated at 90 0C for 5 hr, then was cooled to room temperature and diluted with EtOAc (300 mL). The mixture was filtered through a pad of silica gel and the filtrate was concentrated in vacuo and the residue recrystallized from MeOH (15 g, 52percent); MS (ES) m/z 229.0 (M + H)+. c. 6-bromo-4H-pyrido[3,2-b][1,4]oxazin-3-one The nitropyridine (38 g, 0.125 mole) was dissolved in glacial AcOH (150 mL), and iron powder (20 g, 0.36 mole) was added. The mixture was mechanically stirred and heated at 90 0C for 5 hr, then was cooled to room temperature and diluted with EtOAc (300 mL). The mixture was filtered through a pad of silica gel and the filtrate was concentrated in vacuo and the residue recrystallized from MeOH (15 g, 52percent): LCMS (ES) m/z229.0 (M + H)+. |
52% | at 90℃; for 5 h; | Ethyl (6-bromo-2-nitro-pyridin-3-yloxy)acetate (38 g, 0.125 mole) was dissolved in glacial AcOH (150 mL), and iron powder (20 g, 0.36 mole) was added. The mixture was mechanically stirred and heated at 90 0C for 5 hr, then was cooled to room temperature and diluted with EtOAc (300 mL). The mixture was filtered through a pad of silica gel and the filtrate was concentrated in vacuo and the residue recrystallized from MeOH (15 g,52percent): MS (ES) m/z 229.0 (M + H)+ |
30% | With iron In acetic acid at 90℃; for 1.5 h; | A suspension of the crude D4 and iron powder (162 g, 2.90 mol) in acetic acid (1.2 L) was heated at 90 ° C for 1.5 hours. After dilution of the mixture with EtOAc (2.4 L), the resulting precipitates were filtered off. The filtrate was concentrated under reduced pressure. Flash column chromatography (hexane/EtOAc = 2: 1) of the residue gave D5 (69.0 g, 30percent). 1H NMR (400 MHz, CDC13) (54.67 (s, 2H), 7.10 (d, J= 8.8 Hz, 1H), 7.14 (d, J= 8.8 Hz, 1H), 8.01 (brs, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: With borane-THF In tetrahydrofuran at 90℃; for 1.5 h; Stage #2: With methanol In tetrahydrofuran at 90℃; for 0.333333 h; |
Step 4 To a solution of Compound (9) (3.12 g, 13.7 mmol) in tetrahydrofuran (50 mL), borane-tetrahydrofuran complex (33 mL, 33.0 mmol) was added at room temperature. The solution was then stirred at 90°C for 1.5 hours. Methanol (2.0 mL) was added to the reaction solution, and then the mixture was stirred at 90°C for 20 minutes. The reaction solution was concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with aqueous saturated sodium bicarbonate, dried with anhydrous magnesium sulfate, and then concentrated in vacuo to yield subject compound (10) (3.17 g, 100percent) as a yellow powder.1H-NMR (DMSO-d6) 57.04 (1H, br s), 6.69 (1H, d, J = 7.8 Hz), 6.40 (1H, d, J = 7.8 Hz), 3.91 (2H, t, J = 4.2Hz), 3.19-3.23 (2H, m) LC/MS (Method A): 1.44 min, [M+H]+ = 215.2. |
99% | With diborane In tetrahydrofuran for 1 h; Cooling with ice; Reflux | Under ice bath conditions, Borane in tetrahydrofuran (5.5 mL, 5.5 mmol, 1.0 M) Add dropwise to compound 3.2 (500 mg, 2.19 mmol) In a solution of tetrahydrofuran (25 mL), The reaction system was stirred under reflux with heating for 1 hour. The reaction was then carefully quenched with methanol (10 drops) under reflux. The mixture was cooled to room temperature and concentrated under reduced pressure to remove solvent. The residue was chromatographed on silica gel ( petroleum ether / ethyl acetate = 5/1) Purification afforded compound 23.1 (470 mg, yield: 99percent) It is a white solid. |
87% | With dimethylsulfide borane complex; potassium carbonate In tetrahydrofuran at 70℃; for 0.25 h; Inert atmosphere | Part IV- Synthesis of 6-Bromo-3,4-dihydro-2H-pyrido[3,2-b] [1,4]oxazine; 6-Bromo-4H-pyrido[3,2-b][1,4]oxazin-3-one (1.35 g, 5.89 mmol) was dissolved inTHF (40 mL). Boranedimethylsulphide complex (2.0 Min THF, 5.89 mL, 11.79 mmol) wasadded and the resulting mixture heated to 70 °C under nitrogen for 15 minutes. Next, thereaction mixture was cooled to room temperature, quenched with methanol ( ~5 mL ), and then dried under vacuum to obtain a white solid. The crude material was dissolved indichloromethane and washed with H20. The aqueous phase was discarded and the organicphase was dried under vacuum to give 6-bromo-3,4-dihydro-2H-pyrido[3,2-b ][1,4]oxazine.Yield: 1.1 g (87percent). LCMS (ESI): calc. C7H7BrN20 = 214, 216; obs. M+H = 215, 217. |
[ 959992-62-2 ]
6-Bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine
Similarity: 0.88
[ 122450-96-8 ]
7-Bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one
Similarity: 0.82
[ 916737-77-4 ]
6-Bromo-3-methoxypyridin-2-amine
Similarity: 0.75
[ 894852-01-8 ]
7-Bromo-2,2-dimethyl-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one
Similarity: 0.72
[ 25218-99-9 ]
N-(6-Bromopyridin-2-yl)acetamide
Similarity: 0.71
[ 20348-09-8 ]
2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one
Similarity: 0.86
[ 122450-96-8 ]
7-Bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one
Similarity: 0.82
[ 31354-48-0 ]
N-(3-Hydroxypyridin-2-yl)acetamide
Similarity: 0.73
[ 894852-01-8 ]
7-Bromo-2,2-dimethyl-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one
Similarity: 0.72
[ 25218-99-9 ]
N-(6-Bromopyridin-2-yl)acetamide
Similarity: 0.71
[ 959992-62-2 ]
6-Bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine
Similarity: 0.88
[ 20348-09-8 ]
2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one
Similarity: 0.86
[ 122450-96-8 ]
7-Bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one
Similarity: 0.82
[ 20348-23-6 ]
3,4-Dihydro-2H-pyrido[3,2-b]-1,4-oxazine
Similarity: 0.74
[ 894852-01-8 ]
7-Bromo-2,2-dimethyl-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one
Similarity: 0.72