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CAS No. : | 1383735-65-6 | MDL No. : | MFCD23162252 |
Formula : | C8H6BrN3O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DXLKIGFFFNFTHS-UHFFFAOYSA-N |
M.W : | 240.06 | Pubchem ID : | 71128531 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 51.72 |
TPSA : | 47.78 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) : | -6.94 cm/s |
Log Po/w (iLOGP) : | 2.01 |
Log Po/w (XLOGP3) : | 1.16 |
Log Po/w (WLOGP) : | 1.85 |
Log Po/w (MLOGP) : | 1.46 |
Log Po/w (SILICOS-IT) : | 1.43 |
Consensus Log Po/w : | 1.58 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.51 |
Solubility : | 0.75 mg/ml ; 0.00312 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.76 |
Solubility : | 4.19 mg/ml ; 0.0174 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.91 |
Solubility : | 0.297 mg/ml ; 0.00124 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.88 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | |
Hazard Statements: | H315-H319 | Packing Group: | |
GHS Pictogram: |
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* 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 |
---|---|---|
86% | With water; sodium hydroxide In tetrahydrofuran; methanol at 27℃; for 5 h; | To a solution of 1 -(6-bromo- 1 H-pyrazolo [4,3-b]pyridin- 1 -yl)ethanone (1.4 g, 5.9 mmol) in tetrahydrofuran (20 mL) and methanol (15 mL) was added a solution of sodium hydroxide (0.71 g, 18 mmol) in water (5 mL) at 27 °C. After 5 h, the reaction was neutralized with hydrogen chloride acid (2 mol/L, 10 mL), and the resulting mixture was extracted withethyl acetate (3 x 50 mL). The collected organic extracts were concentrated in vacuo. Purification by flash column chromatography (1 5—30percent ethyl acetate in petroleum ether) afforded 6-bromo-1H-pyrazolo[4,3-b]pyridine (1.0 g, 86percent yield). 1H NMR (400 MHz, Chloroform-d) ö: 10.46 (brs, 1 H), 8.58 (s, 1 H), 8.25 (s, 1 H), 7.98 (s, 1 H). |
86% | With water; sodium hydroxide In tetrahydrofuran; methanol at 27℃; for 5 h; Inert atmosphere | To a solution of 1-(6-bromo-1H-pyrazolo[4,3-b]pyridin-1-yl)ethanone (1.4 g, 5.9 mmol) in tetrahydrofuran (20 mL) and methanol (15 mL) was added a solution of sodium hydroxide (0.71 g, 18 mmol) in water (5 mL) at 27° C. After 5 h, the reaction was neutralized with hydrogen chloride acid (2 mol/L, 10 mL), and the resulting mixture was extracted with ethyl acetate (3*50 mL). The collected organic extracts were concentrated in vacuo. Purification by flash column chromatography (15→30percent ethyl acetate in petroleum ether) afforded 6-bromo-1H-pyrazolo[4,3-b]pyridine (1.0 g, 86percent yield). 1H NMR (400 MHz, Chloroform-d) δ 10.46 (brs, 1H), 8.58 (s, 1H), 8.25 (s, 1H), 7.98 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: glacial acetic acid; iron(0) / 2 h / Reflux 2.1: triethylamine / dichloromethane / 18 h 2.2: 1 h 3.1: acetic anhydride; anhydrous potassium acetate; glacial acetic acid; isopentyl nitrite / toluene / 3 h / Reflux | ||
Multi-step reaction with 3 steps 1: iron(0); ammonia hydrochloride / lithium hydroxide monohydrate; ethanol / 0.17 h / 90 °C 2: glacial acetic acid / 20 °C 3: acetic anhydride; isopentyl nitrite; anhydrous potassium acetate / toluene / 90 °C / Inert atmosphere | ||
Multi-step reaction with 3 steps 1: iron(0); ammonia hydrochloride / ethanol; lithium hydroxide monohydrate / 0.17 h / 90 °C 2: glacial acetic acid / 20 °C 3: acetic anhydride; isopentyl nitrite; anhydrous potassium acetate / toluene / 90 °C / Inert atmosphere |
Multi-step reaction with 3 steps 1: iron(0); ammonia hydrochloride / ethanol; lithium hydroxide monohydrate / 0.17 h / 90 °C 2: glacial acetic acid / 20 °C 3: isopentyl nitrite; anhydrous potassium acetate; acetic anhydride / toluene / 90 °C / Inert atmosphere | ||
Multi-step reaction with 3 steps 1: iron(0); ammonia hydrochloride; lithium hydroxide monohydrate / ethanol / 0.17 h / 90 °C 2: glacial acetic acid / 20 °C 3: anhydrous potassium acetate; isopentyl nitrite / toluene / 90 °C / Inert atmosphere | ||
Multi-step reaction with 3 steps 1.1: ammonia hydrochloride; iron(0) / lithium hydroxide monohydrate; ethanol / 3 h / 80 °C 2.1: pyridine / dichloromethane / 16 h / 80 °C 3.1: anhydrous potassium acetate / toluene / 0.5 h / 80 °C / Inert atmosphere 3.2: 18 h / 80 °C | ||
Multi-step reaction with 3 steps 1.1: ammonia hydrochloride; iron(0) / lithium hydroxide monohydrate; ethanol / 3 h / 80 °C / Inert atmosphere 2.1: pyridine / dichloromethane / 16 h / 80 °C / Inert atmosphere 3.1: anhydrous potassium acetate / toluene / 0.5 h / 80 °C / Inert atmosphere 3.2: 18 h / 80 °C / Inert atmosphere | ||
Multi-step reaction with 3 steps 1.1: ammonia hydrochloride; iron(0) / lithium hydroxide monohydrate; ethanol / 2 h / Reflux 2.1: triethylamine / dichloromethane / 24 h / 20 °C 3.1: glacial acetic acid; anhydrous potassium acetate; acetic anhydride / toluene / Reflux 3.2: 2 h / Reflux | ||
Multi-step reaction with 3 steps 1: iron(0); ammonia hydrochloride / methanol; lithium hydroxide monohydrate / 2 h / 80 °C 2: anhydrous potassium acetate / chloroform / 1 h / 60 °C 3: potassium carbonate; isopentyl nitrite; 18-crown-6 ether / chloroform / 12 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 18 h 1.2: 1 h 2.1: acetic anhydride; anhydrous potassium acetate; glacial acetic acid; isopentyl nitrite / toluene / 3 h / Reflux | ||
Multi-step reaction with 2 steps 1: glacial acetic acid / 20 °C 2: acetic anhydride; isopentyl nitrite; anhydrous potassium acetate / toluene / 90 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: glacial acetic acid / 20 °C 2: acetic anhydride; isopentyl nitrite; anhydrous potassium acetate / toluene / 90 °C / Inert atmosphere |
Multi-step reaction with 2 steps 1: glacial acetic acid / 20 °C 2: isopentyl nitrite; anhydrous potassium acetate; acetic anhydride / toluene / 90 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: glacial acetic acid / 20 °C 2: anhydrous potassium acetate; isopentyl nitrite / toluene / 90 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1.1: pyridine / dichloromethane / 16 h / 80 °C 2.1: anhydrous potassium acetate / toluene / 0.5 h / 80 °C / Inert atmosphere 2.2: 18 h / 80 °C | ||
Multi-step reaction with 2 steps 1.1: pyridine / dichloromethane / 16 h / 80 °C / Inert atmosphere 2.1: anhydrous potassium acetate / toluene / 0.5 h / 80 °C / Inert atmosphere 2.2: 18 h / 80 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 24 h / 20 °C 2.1: glacial acetic acid; anhydrous potassium acetate; acetic anhydride / toluene / Reflux 2.2: 2 h / Reflux | ||
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 12 h / 150 °C 2: acetic anhydride; glacial acetic acid; anhydrous potassium acetate; 3-methyl-1-nitrobutane / toluene / 5 h / 90 °C | ||
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 12 h / 150 °C 2: glacial acetic acid; anhydrous potassium acetate; acetic anhydride / toluene / 5 h / 90 °C | ||
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 20 °C 2: acetic anhydride; anhydrous potassium acetate / toluene / 0.33 h / 120 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: anhydrous potassium acetate / chloroform / 1 h / 60 °C 2: potassium carbonate; isopentyl nitrite; 18-crown-6 ether / chloroform / 12 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With 18-crown-6 ether; potassium carbonate; isopentyl nitrite In chloroform at 60℃; for 12h; | 4.1.18. 1-(6-bromo-1H-pyrazolo[4,3-b]pyridin-1-yl)ethan-1-one (18) Intermediate 17 (56.7 mmol, 1.0 equiv) was added to 100 mLchloroform, followed by isoamyl nitrite (9.2 mL, 68.0 mmol, 1.2 equiv),18-crown-6 (1.5 g, 56.7 mmol, 0.1 equiv), potassium carbonate (19.5 g,141.8 mmol, 2.5 equiv), and the reaction was stirred at 60 C for 12 h.After the reaction was completed, the reaction liquid was concentratedunder reduced pressure, and the crude silica gel was stirred for sample.Pooled sample was separated on a 100 g flashmaster personal + column(mobile phase system PE/EA = 80:20). The target product 18 (10.2 g)was obtained, yield 75%. 1H NMR (400 MHz, DMSO-d6) δ: 8.67 (d, J =1.9 Hz, 1H), 8.45 (d, J = 1.6 Hz, 2H), 2.74 (s, 3H). |
75% | With 18-crown-6 ether; potassium carbonate; isopentyl nitrite In chloroform at 60℃; for 12h; | 4.1.18. 1-(6-bromo-1H-pyrazolo[4,3-b]pyridin-1-yl)ethan-1-one (18) Intermediate 17 (56.7 mmol, 1.0 equiv) was added to 100 mLchloroform, followed by isoamyl nitrite (9.2 mL, 68.0 mmol, 1.2 equiv),18-crown-6 (1.5 g, 56.7 mmol, 0.1 equiv), potassium carbonate (19.5 g,141.8 mmol, 2.5 equiv), and the reaction was stirred at 60 C for 12 h.After the reaction was completed, the reaction liquid was concentratedunder reduced pressure, and the crude silica gel was stirred for sample.Pooled sample was separated on a 100 g flashmaster personal + column(mobile phase system PE/EA = 80:20). The target product 18 (10.2 g)was obtained, yield 75%. 1H NMR (400 MHz, DMSO-d6) δ: 8.67 (d, J =1.9 Hz, 1H), 8.45 (d, J = 1.6 Hz, 2H), 2.74 (s, 3H). |
55% | With anhydrous potassium acetate; acetic anhydride; isopentyl nitrite In toluene at 90℃; Inert atmosphere; | 9.3 Step 3. 1-(6-bromopyrazolo[4,3-b]pyridin-1-yl)-ethanone A mixture of N- (5-bromo-2-methyl-pyridin-3-yl)-acetamide (3.5 g, 1 5.28 mmol, 1 .00 equiv), isopentyl nitrite (4 g, 34.73 mmol, 2.27 equiv ), potassium acetate (20 g), and acetic anhydride (30 mL) in toluene ( 1 0 mL) was stirred under nitrogen overnight at 90 °C. The reaction mixture was cooled to rt and the solid material was removed by filtration. The filtrate was concentrated under vacuum and the residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether ( 1 :5) to give in 2 g (55%) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT= 1 .44 min, m/z = 240.0; 242.0 [M · H]-. |
55% | With anhydrous potassium acetate; acetic anhydride; isopentyl nitrite In toluene at 90℃; Inert atmosphere; | 9.3 Step 3. 1-(6-bromopyrazolo[4,3-b]pyridin-1-yl)-ethanone A mixture of N- (5-bromo-2-methyl-pyridin-3-yl)-acetamide (3.5 g, 1 5.28 mmol, 1 .00 equiv), isopentyl nitrite (4 g, 34.73 mmol, 2.27 equiv ), potassium acetate (20 g), and acetic anhydride (30 mL) in toluene ( 1 0 mL) was stirred under nitrogen overnight at 90 °C. The reaction mixture was cooled to rt and the solid material was removed by filtration. The filtrate was concentrated under vacuum and the residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether ( 1 :5) to give in 2 g (55%) of the title compound as a light yellow solid. LC MS (Method I, ESI): RT= 1 .44 min, m z = 240.0; 242.0 [M · H]*. |
55% | With anhydrous potassium acetate; acetic anhydride; isopentyl nitrite In toluene at 90℃; Inert atmosphere; | 9.3 Step 3. 1-(6-Bromo-pyrazolo[4,3-blpyridin-1-yl)-ethanone. [0202] Step 3. 1-(6-Bromo-pyrazolo[4,3-blpyridin-1-yl)-ethanone. A mixture of N-(5- bromo-2-methyl-pyridin-3-yl)-acetamide (3.5 g, 15.28 mmol, 1.00 equiv), isopentyl nitrite (4 g, 34.73 mmol, 2.27 equiv), potassium acetate (20 g), and acetic anhydride (30 mL) in toluene (150 mL) was stirred under nitrogen overnight at 90 °C. The reaction mixture was cooled to rt and the solid material was removed by filtration. The filtrate was concentrated under vacuum and the residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1:5) to give in 2 g (55%) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT= 1.44 mm, m/z = 240.0; 242.0 [M+H]. |
55% | With anhydrous potassium acetate; isopentyl nitrite In toluene at 90℃; Inert atmosphere; | Step 3. l-(6-Bromo-pyrazolor4,3-blpyridin-l-yl)-ethanone 0210] Step 3. l-(6-Bromo-pyrazolor4,3-blpyridin-l-yl)-ethanone. A mixture of N-(5- bromo-2-methyl-pyridin-3-yl)-acetamide (3.5 g, 15.28 mmol, 1.00 equiv), isopentyl nitrite (4 g, 34.73 mmol, 2.27 equiv), potassium acetate (20 g), and acetic anhydride (30 mL) in toluene (150 mL) was stirred under nitrogen overnight at 90 °C. The reaction mixture was cooled to rt and the solid material was removed by filtration. The filtrate was concentrated under vacuum and the residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1:5) to give in 2 g (55%) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT= 1.44 min, m/z = 240.0; 242.0 [M+H]+. |
48% | Stage #1: N-(5-bromo-2-methylpyridin-3-yl)acetamide With anhydrous potassium acetate In toluene at 80℃; for 0.5h; Inert atmosphere; Stage #2: With 2-Methyl-2-nitropropane; acetic anhydride In toluene at 80℃; for 18h; Inert atmosphere; | 1.3 Synthesis of 1-(6-bromo-1H-pyrazolo[4,3-b]pyridin-1-yl)ethanone A solution of N-(5-bromo-2-methylpyridin-3-yl)acetamide (2.8 g, 12 mmol) and potassium acetate (3.59 g, 36.6 mmol) in toluene (50 mL) was heated at 80° C. under nitrogen. After 30 min, 2-methyl-2-nitropropane (3.77 g, 36.6 mmol) and acetic anhydride (3.73 g, 36.6 mmol) were added, and the resulting mixture was stirred at 80° C. for another 18 h. The reaction mixture was concentrated in vacuo, and the residue was diluted with water (50 mL). The aqueous mixture was extracted with ethyl acetate (3*60 mL). The collected organic extractions were concentrated in vacuo. Purification by flash column chromatography (5→10% ethyl acetate in petroleum ether) afforded 1-(6-bromo-1H-pyrazolo[4,3-b]pyridin-1-yl)ethanone (1.4 g, 48.% yield). 1H NMR (400 MHz, Chloroform-d) δ 8.90 (s, 1H), 8.75 (s, 1H), 8.32 (s, 1H), 2.79 (s, 3H). |
With anhydrous potassium acetate; acetic anhydride; glacial acetic acid; isopentyl nitrite In toluene for 3h; Reflux; | To a solution of T-5 (13.14 g, 57.36 mmol) in toluene (200 mL) is added acetic anhydride (16.50 mL, 174.5 mmol), acetic acid (16.50 mL, 288.2 mmol) and potassium acetate (12.30 g, 125.3 mmol). The mixture is warmed at reflux and isoamyl nitrite (10.0 mL, 71.5 mmol) is added. After 3 hours, the reaction is concentrated to provide without isolation T-6. The residue is diluted with methanol (250 mL) and K2CO3 (32.0 g, 188 mmol) is added and the mixture is warmed at reflux. After 1 hour, the reaction is poured into water and extracted with EtOAc (3 x 150 mL). The combined organic layers are washed with brine (2 x 50 mL), dried over magnesium sulfate, filtered through a pad of silica gel and filter agent and concentrated. The solid is triturated with Et2O to provide T-7. The filtrate is purified on silica gel using a gradient of 25-100% EtOAc in hexanes and then 5% methanol in ethyl acetate. The material from the column is triturated with ether-heptane to provide T-7. | |
Stage #1: N-(5-bromo-2-methylpyridin-3-yl)acetamide With anhydrous potassium acetate; acetic anhydride; glacial acetic acid In toluene Reflux; Stage #2: With isopentyl nitrite In toluene for 2h; Reflux; | 172.5 [0005711 Step 5: Synthesis of 1-(6-bromo-1H-pyrazolo [4,3-bi pyridin-1-yl)ethanone (6): [0005721 To a stirred solution of compoundS (1.35 g,1 eq) in toluene (15 mE), potassiumacetate (1.27 g, 2.2 eq), acetic anhydride (1.67 mL, 3 eq) and acetic acid (1.68 mL, 5 eq) was heated to reflux followed by the addition of isoamyl nitrite (1 mL, 1.25 eq) and refluxed for 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was quenched with saturated sodium bicarbonate solution and extracted with ethyl acetate (2 X 50 mL). Combined organic extracts were dried over anhydrous sodium sulfate and evaporated under reduced pressure to afford the title compound 6. LCMS (mlz): 242.15 (M + 2). | |
With 3-methyl-1-nitrobutane; anhydrous potassium acetate; acetic anhydride; glacial acetic acid In toluene at 90℃; for 5h; | B [B] 1- (6-Bromo-1H-pyrazolo [4 3-b] pyridin-1-yl) ethanone [B] 1- (6-Bromo-1H-pyrazolo [4 3-b] pyridin-1-yl) ethanone[0265][0266]To a solution of N- (5-bromo-2-methylpyridin-3-yl) acetamide (14 g 61.1 mmol) in toluene (200 mL) was added Ac2O (21 mL 183 mmol) AcOH (21 mL 300 mmol) and KOAc (11.7 g 120 mmol) . The resulting reaction mixture was warmed up to 90 added CHMe2CH2CH2NO2(110 mL) and stirred at 90 for 5 h. After cooling to room temperature the mixture was poured into water basified with aq. NaHCO3solution and extracted with EtOAc (50 mL x 6) . The combined organic layers were dried over anhy. MgSO4 filtered and concentrated in vacuo to give a crude title compound (6.5 g 44.5yield) as a solid. MS 241.06 [M+H]+. | |
50 mg | Stage #1: N-(5-bromo-2-methylpyridin-3-yl)acetamide With anhydrous potassium acetate; acetic anhydride In toluene at 120℃; for 0.333333h; Inert atmosphere; Stage #2: With isopentyl nitrite In toluene | 11.2 Step 2: 1-(6-bromopyrazolo[4,3-b]pyridin-1-yl)ethanone (C11-3) Intermediate C11-2 (100 mg, 0.44 mmol), KOAc (94 mg, 0.96 mmol) and Ac2O (265 mg, 1.31 mmol) were dissolved in toluene (10 mL) under N2, and the mixture was refluxed at 120 °C for 20 min. Isopentyl nitrite (64 mg, 0.55 mmol) was added via a syringe. The reaction continued overnight. TLC was used to monitor the reaction and the reaction was incomplete. The mixture was extracted with EtOAc (20 mL). The organic layer was collected, dried over anhydrous Na2SO4, filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (petroleum ether/EtOAc = 5:1) to afford the title compound as a yellow solid (50 mg, 48%). NMR (400 MHz, CDCl3) d 8.91 (s, 1H), 8.75 (s, 1H), 8.32 (s, 1H), 2.80 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With water; sodium hydroxide; In tetrahydrofuran; methanol; at 27℃; for 5h; | To a solution of 1 -(6-bromo- 1 H-pyrazolo [4,3-b]pyridin- 1 -yl)ethanone (1.4 g, 5.9 mmol) in tetrahydrofuran (20 mL) and methanol (15 mL) was added a solution of sodium hydroxide (0.71 g, 18 mmol) in water (5 mL) at 27 C. After 5 h, the reaction was neutralized with hydrogen chloride acid (2 mol/L, 10 mL), and the resulting mixture was extracted withethyl acetate (3 x 50 mL). The collected organic extracts were concentrated in vacuo. Purification by flash column chromatography (1 5-30% ethyl acetate in petroleum ether) afforded 6-bromo-1H-pyrazolo[4,3-b]pyridine (1.0 g, 86% yield). 1H NMR (400 MHz, Chloroform-d) oe: 10.46 (brs, 1 H), 8.58 (s, 1 H), 8.25 (s, 1 H), 7.98 (s, 1 H). |
86% | With water; sodium hydroxide; In tetrahydrofuran; methanol; at 27℃; for 5h;Inert atmosphere; | To a solution of 1-(6-bromo-1H-pyrazolo[4,3-b]pyridin-1-yl)ethanone (1.4 g, 5.9 mmol) in tetrahydrofuran (20 mL) and methanol (15 mL) was added a solution of sodium hydroxide (0.71 g, 18 mmol) in water (5 mL) at 27 C. After 5 h, the reaction was neutralized with hydrogen chloride acid (2 mol/L, 10 mL), and the resulting mixture was extracted with ethyl acetate (3*50 mL). The collected organic extracts were concentrated in vacuo. Purification by flash column chromatography (15?30% ethyl acetate in petroleum ether) afforded 6-bromo-1H-pyrazolo[4,3-b]pyridine (1.0 g, 86% yield). 1H NMR (400 MHz, Chloroform-d) delta 10.46 (brs, 1H), 8.58 (s, 1H), 8.25 (s, 1H), 7.98 (s, 1H). |
With methanol; potassium carbonate; for 1h;Reflux; | To a solution of T-5 (13.14 g, 57.36 mmol) in toluene (200 mL) is added acetic anhydride (16.50 mL, 174.5 mmol), acetic acid (16.50 mL, 288.2 mmol) and potassium acetate (12.30 g, 125.3 mmol). The mixture is warmed at reflux and isoamyl nitrite (10.0 mL, 71.5 mmol) is added. After 3 hours, the reaction is concentrated to provide without isolation T-6. The residue is diluted with methanol (250 mL) and K2CO3 (32.0 g, 188 mmol) is added and the mixture is warmed at reflux. After 1 hour, the reaction is poured into water and extracted with EtOAc (3 x 150 mL). The combined organic layers are washed with brine (2 x 50 mL), dried over magnesium sulfate, filtered through a pad of silica gel and filter agent and concentrated. The solid is triturated with Et2O to provide T-7. The filtrate is purified on silica gel using a gradient of 25-100% EtOAc in hexanes and then 5% methanol in ethyl acetate. The material from the column is triturated with ether-heptane to provide T-7. |
With methanol; potassium carbonate; for 1h;Reflux; | [0005731 To a stirred solution of compound 6 (1.25 g, 1 eq) in methanol (15 mL), K2C03 (2.15 g, 3 eq) was added and heated to reflux for 1 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was evaporated to dryness. The residue was dissolved in water and extracted with ethyl acetate (2 X 25 mE). Combined organic extracts were dried over anhydrous sodium sulfate and evaporated under reduced pressure to afford the title compound 7. LCMS (mlz): 199.90 (M+ 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate; methanol / 1 h / Reflux 2: N-ethyl-N,N-diisopropylamine / bis(benzonitrile)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene / 4 h / 135 °C / 11251.1 Torr 3: potassium carbonate / cis-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide / N,N-dimethyl-formamide / 3 h / 130 °C / microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate; methanol / 1 h / Reflux 2: N-ethyl-N,N-diisopropylamine / bis(benzonitrile)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene / 4 h / 135 °C / 11251.1 Torr 3: potassium carbonate / cis-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide / N,N-dimethyl-formamide / 3 h / 130 °C / microwave irradiation 4: hydrogenchloride; hydrogen / platinum(IV) oxide hydrate / 1,4-dioxane; ethanol / 18 h / 760.05 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate; methanol / 1 h / Reflux 2: N-ethyl-N,N-diisopropylamine / bis(benzonitrile)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene / 4 h / 135 °C / 11251.1 Torr 3: potassium carbonate / cis-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide / N,N-dimethyl-formamide / 3 h / 130 °C / microwave irradiation 4: lithium aluminium tetrahydride / tetrahydrofuran / 18 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium carbonate; methanol / 1 h / Reflux 2: N-ethyl-N,N-diisopropylamine / bis(benzonitrile)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene / 4 h / 135 °C / 11251.1 Torr 3: potassium carbonate / cis-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide / N,N-dimethyl-formamide / 3 h / 130 °C / microwave irradiation 4: hydrogenchloride; hydrogen / platinum(IV) oxide hydrate / 1,4-dioxane; ethanol / 18 h / 760.05 Torr 5: sodium hydrogencarbonate / dichloromethane; toluene; water / 1 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: potassium carbonate; methanol / 1 h / Reflux 2: N-ethyl-N,N-diisopropylamine / bis(benzonitrile)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene / 4 h / 135 °C / 11251.1 Torr 3: potassium carbonate / cis-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide / N,N-dimethyl-formamide / 3 h / 130 °C / microwave irradiation 4: hydrogenchloride; hydrogen / platinum(IV) oxide hydrate / 1,4-dioxane; ethanol / 18 h / 760.05 Torr 5: sodium hydrogencarbonate / dichloromethane; toluene; water / 1 h / 0 °C 6: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: potassium carbonate; methanol / 1 h / Reflux 2.1: N-ethyl-N,N-diisopropylamine / bis(benzonitrile)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene / 4 h / 135 °C / 11251.1 Torr 3.1: potassium carbonate / cis-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide / N,N-dimethyl-formamide / 3 h / 130 °C / microwave irradiation 4.1: hydrogenchloride; hydrogen / platinum(IV) oxide hydrate / 1,4-dioxane; ethanol / 18 h / 760.05 Torr 5.1: sodium hydrogencarbonate / dichloromethane; toluene; water / 1 h / 0 °C 6.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h 7.1: sodium hydroxide; water / methanol / 4 h 7.2: pH 4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: potassium carbonate; methanol / 1 h / Reflux 2.1: N-ethyl-N,N-diisopropylamine / bis(benzonitrile)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene / 4 h / 135 °C / 11251.1 Torr 3.1: potassium carbonate / cis-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide / N,N-dimethyl-formamide / 3 h / 130 °C / microwave irradiation 4.1: hydrogenchloride; hydrogen / platinum(IV) oxide hydrate / 1,4-dioxane; ethanol / 18 h / 760.05 Torr 5.1: sodium hydrogencarbonate / dichloromethane; toluene; water / 1 h / 0 °C 6.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h 7.1: sodium hydroxide; water / methanol / 4 h 7.2: pH 4 8.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 18 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With bis-triphenylphosphine-palladium(II) chloride; triethylamine at 100℃; | 9.4 Step 4. 1H-Pyrazolo[4.3-b]pyridine-6-carboxylic acid methyl ester. A mixture of 1-(6-bromo-pyrazolo[4,3-b]pyridin- 1-yl)-ethanone (2 g, 8.33 mmol, 1 .00 equiv), bis(triphenylphosphine)palladium(II) dichloride ( 1 g, 1 42 mmol, 0.1 7 equiv), and triethylamine (2.5 mL) in methanol (70 mL) was stirred overn ight under carbon monoxide ( 10 atmospheres) at 100 "C in a 1 00 mL pressure reactor The reaction mixture was cooled to rt and the solid material was removed by filtration. The filtrate was concentrated under vacuum and the residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1 :5) to afford 0.8 g (54%) of the title compound as a light yellow solid. TLC: 1 : 1 ethyl acetate/petroleum ether, Rf= 0.2. |
54% | With bis-triphenylphosphine-palladium(II) chloride; triethylamine at 100℃; Sealed tube; | 9.4 Step 4. 1H-Pyrazolo[4.3-b]pyridine-6-carboxylic acid methyl ester. A mixture of l -(6-bromo-pyrazolo[4,3 -b]pyridin- l -yl)-ethanone (2 g, 8.33 mmol, 1 .00 equiv), bis(triphenylphosphine)palladium(II) dichloride ( 1 g, 1 42 mmol, 0.1 7 equiv), and triethylamine (2.5 mL) in methanol (70 mL) was stirred overn ight under carbon monoxide ( 10 atmospheres) at 100 "C in a 1 00 mL pressure reactor The reaction mixture was cooled to rt and the solid material was removed by filtration. The filtrate was concentrated under vacuum and the residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1 :5) to afford 0.8 g (54%) of the title compound as a light yellow solid. TLC: 1 : 1 ethyl acetate/petroleum ether, Rf= 0.2. |
With bis-triphenylphosphine-palladium(II) chloride; triethylamine at 100℃; | 9.4 Step 4. 1H-Pyrazolo[4,3-blpyridine-6-carboxylic acid methyl ester. [0203] Step 4. 1H-Pyrazolo[4,3-blpyridine-6-carboxylic acid methyl ester. A mixture of 1-(6-bromo-pyrazolo[4,3-b]pyridin-1-yl)-ethanone (2 g, 8.33 mmol, 1.00 equiv), bis(triphenylphosphine)palladium(II) dichloride (1 g, 1.42 mmol, 0.17 equiv), and triethylamine (2.5 mL) in methanol (70 mL) was stirred overnight under carbon monoxide (10 atmospheres) at 100 °C in a 100 mL pressure reactor. The reaction mixture was cooled to rt and the solid material was removed by filtration. The filtrate was concentrated under vacuum and the residue was purified on a silica gel column eluted with ethylacetate/petroleum ether (1:5) to afford 0.8 g (54%) of the title compound as a light yellow solid. TLC: 1:1 ethyl acetate/petroleum ether, Rf = 0.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 100 °C / 7600.51 Torr 2: water; sodium hydroxide / 20 °C | ||
Multi-step reaction with 2 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 100 °C / 7600.51 Torr / Sealed tube 2: water; sodium hydroxide / 20 °C | ||
Multi-step reaction with 2 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 100 °C / 7600.51 Torr 2: sodium hydroxide; water / 20 °C |
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; methanol; triethylamine / 100 °C / 7600.51 Torr 2: sodium hydroxide / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With methanol; bis-triphenylphosphine-palladium(II) chloride; triethylamine at 100℃; | Step 4. lH-Pyrazolor4,3-blpyridine-6-carboxylic acid methyl ester [0211] Step 4. lH-Pyrazolor4,3-blpyridine-6-carboxylic acid methyl ester. A mixture of l-(6-bromo-pyrazolo[4,3-b]pyridin-l-yl)-ethanone (2 g, 8.33 mmol, 1.00 equiv), bis(triphenylphosphine)palladium(II) dichloride (1 g, 1.42 mmol, 0.17 equiv), and triethylamine (2.5 mL) in methanol (70 mL) was stirred overnight under carbon monoxide (10 atmospheres) at 100 °C in a 100 mL pressure reactor. The reaction mixture was cooled to rt and the solid material was removed by filtration. The filtrate was concentrated under vacuum and the residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1:5) to afford 0.8 g (54%) of the title compound as a light yellow solid. TLC: 1: 1 ethyl acetate/petroleum ether, Rf = 0.2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | Stage #1: N-(5-bromo-2-methyl-pyridin-3-yl)-acetamide With potassium acetate In toluene at 80℃; for 0.5h; Inert atmosphere; Stage #2: 2-Methyl-2-nitropropane With acetic anhydride In toluene at 80℃; for 18h; | 1.3 Step 3: Synthesis of 1- (6-bromo- 1 H-pyrazolo [4,3-b]pyridin- 1 -yl)ethanone. A solution of N-(5-bromo-2-methylpyridin-3-yl)acetamide (2.8 g, 12 mmol) and potassium acetate (3.59 g, 36.6 mmol) in toluene (50 mL) was heated at 80 °C under nitrogen. After 30 mi 2-methyl-2-nitropropane (3.77 g, 36.6 mmol) and acetic anhydride (3.73 g,36.6 mmol) were added, and the resulting mixture was stirred at 80 °C for another 18 h. The reaction mixture was concentrated in vacuo, and the residue was diluted with water (50 mL). The aqueous mixture was extracted with ethyl acetate (3 x 60 mL). The collected organic extractions were concentrated in vacuo. Purification by flash column chromatography (5-* 10% ethyl acetate in petroleum ether) afforded1-(6-bromo-1H-pyrazolo[4,3-b]pyridin-1-yl)ethanone (1.4 g, 48.% yield). 1H NMR (400MHz, Chloroform-d) ö: 8.90 (s, 1 H), 8.75 (s, 1 H), 8.32 (s, 1 H), 2.79 (s, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); 2-nitropropane; zinc In N,N-dimethyl acetamide at 90 - 120℃; for 5h; | C [C] 1H-pyrazolo [4 3-b] pyridine-6-carbonitrile [0267] [C] 1H-pyrazolo [4, 3-b] pyridine-6-carbonitrile [0268] [0269] To a stirred solution of 1- (6-bromo-1H-pyrazolo [4, 3-b] pyridin-1-yl) ethanone (6.5 g, 27.04 mmol) in DMA (60 mL) was added Zn (0.416 g, 6.5 mmol), DPPF (1.19 g, 2.08 mmol), Zn (CN) 2 (2.08 g, 17.55 mmol) and Pd2 (dba) 3 (0.97 g, 0.78 mmol). The reaction was warmed up to 90 before iPrNO2 (19.5 mL) was added, and the resulting mixture was stirred at 120 for 5 h. After cooling to room temperature, the mixture was diluted with EtOAc (60 mL) and satd. aq. NaHCO3 solution (100mL). The combined organic layers were dried over anhy. MgSO4, filtered, and concentrated in vacuo to give a crude title compound (0.95 g, 24.4 yield) as a solid. MS 145.1 [M+H] +. 1H NMR (400 MHz, DMSO-d6) δ 8.84 (d, J1.5 Hz, 1H), 8.74 (s, 1H), 8.51 (s, 1H). | |
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); i-propyl nitrite; zinc at 90 - 120℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium acetate; acetic anhydride; acetic acid In toluene at 90℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C 4: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane; ethanol / 2 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C 4: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane; ethanol / 2 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C 4: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane; ethanol / 2 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C 4: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane; ethanol / 2 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C 4: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane; ethanol / 2 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C 4: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane; ethanol / 2 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C 4: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane; ethanol / 2 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C 4: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane; ethanol / 2 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C 4: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane; ethanol / 2 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C 4: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane; ethanol / 2 h / 80 °C / Inert atmosphere 5: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Cs2CO3 / 1,4-dioxane / 100 - 103 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C 4: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane; ethanol / 2 h / 80 °C / Inert atmosphere 5: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Cs2CO3 / 1,4-dioxane / 100 - 103 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C 4: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane; ethanol / 2 h / 80 °C / Inert atmosphere 5: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Cs2CO3 / 1,4-dioxane / 100 - 103 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C 4: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane; ethanol / 2 h / 80 °C / Inert atmosphere 5: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Cs2CO3 / 1,4-dioxane / 100 - 103 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C 4: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane; ethanol / 2 h / 80 °C / Inert atmosphere 5: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Cs2CO3 / 1,4-dioxane / 100 - 103 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C 4: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane; ethanol / 2 h / 80 °C / Inert atmosphere 5: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Cs2CO3 / 1,4-dioxane / 100 - 103 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C 4: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane; ethanol / 2 h / 80 °C / Inert atmosphere 5: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Cs2CO3 / 1,4-dioxane / 100 - 103 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C 4: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane; ethanol / 2 h / 80 °C / Inert atmosphere 5: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Cs2CO3 / 1,4-dioxane / 100 - 103 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C 4: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane; ethanol / 2 h / 80 °C / Inert atmosphere 5: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Cs2CO3 / 1,4-dioxane / 100 - 103 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C 4: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane; ethanol / 2 h / 80 °C / Inert atmosphere 5: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Cs2CO3 / 1,4-dioxane / 100 - 103 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C 4: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane; ethanol / 2 h / 80 °C / Inert atmosphere 5: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Cs2CO3 / 1,4-dioxane / 100 - 103 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C 4: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane; ethanol / 2 h / 80 °C / Inert atmosphere 5: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Cs2CO3 / 1,4-dioxane / 100 - 103 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 20 °C 2: potassium carbonate / acetonitrile / 3 h / 80 °C 3: anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane / 12 h / 90 °C 4: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane; ethanol / 2 h / 80 °C / Inert atmosphere 5: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Cs2CO3 / 1,4-dioxane / 100 - 103 °C / Inert atmosphere |
Tags: 1383735-65-6 synthesis path| 1383735-65-6 SDS| 1383735-65-6 COA| 1383735-65-6 purity| 1383735-65-6 application| 1383735-65-6 NMR| 1383735-65-6 COA| 1383735-65-6 structure
[ 1779130-00-5 ]
1-(3-Bromo-1H-pyrazolo[4,3-b]pyridin-1-yl)ethanone
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1-(3-Bromo-1H-pyrazolo[4,3-b]pyridin-1-yl)ethanone
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1-(1H-Pyrazolo[4,3-b]pyridin-1-yl)ethanone
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Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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