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[ CAS No. 188057-49-0 ]

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Chemical Structure| 188057-49-0
Chemical Structure| 188057-49-0
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Product Details of [ 188057-49-0 ]

CAS No. :188057-49-0 MDL No. :MFCD09859112
Formula : C5H3BrINO Boiling Point : 325.1°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :299.89 g/mol Pubchem ID :-
Synonyms :

Safety of [ 188057-49-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 188057-49-0 ]

  • Downstream synthetic route of [ 188057-49-0 ]

[ 188057-49-0 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 188057-49-0 ]
  • cis-1-propenylboronic acid [ No CAS ]
  • [ 1073633-64-3 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate In 1,4-dioxane; water at 100℃; 17.b (b) 5-Bromo-2-[(lZ)-l-propen-l-yl]-3-pyridinol; A mixture of 5-bromo-2-iodo-3-pyridinol (11.16 g, 37.2 mmol), c-propenyl boronic acid (3.84 g, 44.7 mmol) and potassium carbonate (3.84 g, 149 mmol) in 1,4- dioxane/water (3:1, 320 ml) was degassed by bubbling nitrogen through before addition of tetrakis(triphenylphoshine)palladium(0) (0.860 g, 0.74 mmol). The mixture was heated at 1000C overnight, and then evaporated. The aqueous residue was filtered under suction, washed through with DMF, and the filtrate was evaporated to approx. half volume. The residue was then used crude in the next step (assumed 100% yield). MS (+ve ion electrospray) m/z 214/216 (MH+).
  • 2
  • [ 74115-13-2 ]
  • [ 188057-49-0 ]
YieldReaction ConditionsOperation in experiment
100% With iodine; anhydrous sodium carbonate In water monomer at 25℃; for 3h; Inert atmosphere; 35 Preparative Example 35 5-bromopyridin-3~ol (1.1 g, 6.3 mmol), iodine (1.6 g, 6.3 mmol), Na2C03 (1.4 g, 13.2 g) and 0 (21 mL) were placed into a 100 mL round bottom flask. The mixture was stirred under N2 at 25 °C for 3 h. The mixture was neutralized with 1 M aqueous solution of HCl and extracted with EtOAc (60+40+40 mL). The organic phase was washed with brine (50 mL), dried over MgS04 and filtered. The product was obtained as a brown solid (1.89 g; 100 %). ]H NMR (300 MHz, CDC13) S 8.08 (d, J= 2.1 Hz, 1H), 7.38 (d, J = 2.1 Hz, 1H), 5.39 (s, 1H).
100% With iodine; anhydrous sodium carbonate In water monomer at 20℃; for 3.25h; 17.a Example 17; 4- {3- [(2,3-Dihydro [1 ,4] dioxino [2,3-c] pyridin-7-ylmethyl)amino] -3,4- dihydro-2H-pyrano[3,2-6]pyridin-7-yl}-6-(methyloxy)pyrido[2,3-6]pyrazin-3(4H)- one fumarate; (a) 5-Bromo-2-iodo-3-pyridinol; 5-Bromo-3-pyridinol (25.1 g, 144 mmol) was suspended in water (500ml), sodium carbonate (45.9 g, 433 mmol) was added and the mixture was stirred until a clear solution formed. Iodine (36.6 g, 144 mmol) was added in portions over 2.75h while stirring at room temp. Iodine dissolved more quickly as the reaction progressed, giving a dark brown solution which gradually turned to pale yellow. The mixture was stirred for another 30 min, and then added gradually to 150ml 2M hydrochloric acid. A white precipitate formed. More acid was added as required to bring the final pH to approximately 7. The solid was filtered off, washed with water and dried (5O0C, vacuum) to give the product (43.16g , 100%). MS (+ve ion electrospray) m/z 300/302 (MH+).
91% With iodine; Sodium hydrogenocarbonate In water monomer for 4h; 16.1 1. Synthesis of Intermediate 16-2: To a solution of 5-bromopyridin-3-ol (25 g, 144 mmol, 1.0 equiv) in water (500 mL) were added sodium carbonate (45.9 g, 434 mmol, 3.0 equiv) and I2 (36.6 g, 144 mmol, 1.00 equiv) in portions for a period of 3 h. The mixture was stirred for 1 h and brought to pH 7 with hydrogen chloride (2 N). The resulting precipitate was collected and dried to afford 39 g (91%) of 5-bromo-2-iodopyridin-3-ol as a white solid.
87% With iodine; anhydrous sodium carbonate In water monomer at 25℃; for 3h; 8.1 Step 1. To a solution of 5-bromopyridin-3-ol (5.0 g, 28.7 mmol) in H20 (300 mL) wasadded Na2CO3 (6.1 g, 57.5 mmol) and 12 (7.3 g, 28.7 mmol). The mixture was stirred at 25°C for 3 hrs. The reaction mixture was extracted with EtOAc and the combined organiclayers were washed with brine, dried over Na2 SO4, filtered and concentrated under reducedpressure. The crude residue was purified by silica gel chromatography to give 5-bromo-2-iodopyridin-3-ol (7.5 g, 87% yield). ‘HNMR (400 IVIHz, Chloroform-cl) ppm 8.09 (s,1H)7.39 (s, 1 H).
86% Stage #1: 3-hydroxy-5-bromopyridine With iodine; anhydrous sodium carbonate In water monomer at 20℃; for 2h; Inert atmosphere; Stage #2: With hydrogenchloride In water monomer Inert atmosphere;
81% With iodine; anhydrous sodium carbonate In water monomer at 20℃; for 6h; Inert atmosphere; 258 5-bromo-2-iodopyridin-3-ol 5-bromo-2-iodopyridin-3-ol To a solution of 5-bromopyridin-3-ol (20.00 g, 114.95 mmol) in water (400 mL) was added sodium carbonate (40.00 g, 377.40 mmol) and iodine (30.00 g, 118.20 mmol) at room temperature. The resulting solution was stirred for 6 h at room temperature. After the reaction was done, the pH value of the reaction mixture was adjusted to 3 with hydrogen chloride solution (2 M). Precipitation happened. The precipitates were collected by filtration and dried in oven under vacuum to yield 5-bromo-2-iodopyridin-3-ol as a yellow solid (28.00 g, 81%). 1H NMR (400 MHz, CD3OD, ppm) δ 7.93 (s, 1H), 7.24 (d, J=2.0 Hz, 1H).
81% With iodine; anhydrous sodium carbonate In water monomer at 25℃; for 2h; 1 Take 120.00g (0.690mol) of 3-bromo-5-hydroxypyridine, 2.4L of water, and 219.42g (2.070mol) of sodium carbonate in a flask, add 175.13g (0.690mol) of iodine in batches at 25°C, and continue to react for 2 hours,The reaction was monitored by HPLC, and the remaining amount of raw materials was less than 0.5%; the reaction solution was poured into dilute hydrochloric acid, extracted twice with ethyl acetate, the organic phases were combined, and the solvent was distilled off under reduced pressure.210.00 g of crude product (HPLC purity 93%) was obtained, which was recrystallized with acetic acid and petroleum ether, filtered and dried.167.61 g of compound 1 were obtained (yellow solid, yield 81.0%).
75% With iodine; anhydrous sodium carbonate In water monomer at 25℃; for 3h; Inert atmosphere; 194.1 Step 1: 5-Bromo-2-iodopyridin-3-ol A mixture of 5-bromopyridin-3-ol (10 g, 57.47 mmol), 12 (14.59 g, 57.47 mmol), andNa2CO3 (12.79 g, 120.69 mmol) in H20 (200 mL) was degassed and purged with N2 (3x) andthen the mixture was stirred at 25 °C for 3 hrs under an N2 atmosphere. The reaction mixture was acidified with 1 M HC1 to pH = 5 and extracted with EtOAc (3x). The combined organic layers were dried over Na2SO4, filtered, and concentrated to afford the title compound (13 g, 75%) as a brown solid. ‘H NMR (400 MHz, DMSO-d6) ö 11.40 (s, 1 H), 8.01 (d, J=2. 13 Hz,1 H), 7.30 (d, J=2.13 Hz, 1 H). MS-ESI (m/z) calc’d for C5H4BrINO [M+Hf: 299.8, 301.8. Found 299.8, 301.8.
71% With iodine; anhydrous sodium carbonate In water monomer at 20℃; for 3h; Inert atmosphere;

  • 4
  • [ 625-92-3 ]
  • [ 188057-49-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide; methanol / 2 h / 80 °C / Inert atmosphere; Microwave irradiation 2: boron tribromide / dichloromethane / 48 h / -78 - 20 °C / Inert atmosphere 3: sodium carbonate; iodine / water / 3 h / 20 °C / Inert atmosphere
  • 5
  • [ 50720-12-2 ]
  • [ 188057-49-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: boron tribromide / dichloromethane / 48 h / -78 - 20 °C / Inert atmosphere 2: sodium carbonate; iodine / water / 3 h / 20 °C / Inert atmosphere
  • 6
  • [ 188057-49-0 ]
  • (E)-N'-(2-cyano-6-phenylfuro[3,2-b]pyridin-3-yl)-N,N-dimethylformimidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube
  • 7
  • [ 188057-49-0 ]
  • (E)-N'-(2-cyano-6-p-tolylfuro[3,2-b]pyridin-3-yl)-N,N-dimethylformimidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube
  • 8
  • [ 188057-49-0 ]
  • (E)-N'-(2-cyano-6-(4-methoxyphenyl)furo[3,2-b]pyridin-3-yl)-N,N-dimethylformimidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube
  • 9
  • [ 188057-49-0 ]
  • (E)-N'-(6-(3-chlorophenyl)-2-cyanofuro[3,2-b]pyridin-3-yl)-N,N-dimethylformimidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube
  • 10
  • [ 188057-49-0 ]
  • (E)-N'-(6-(3,4-dichlorophenyl)-2-cyanofuro[3,2-b]pyridin-3-yl)-N,N-dimethylformimidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube
  • 11
  • [ 188057-49-0 ]
  • (E)-N'-(6-(4-chlorophenyl)-2-cyanofuro[3,2-b]pyridin-3-yl)-N,N-dimethylformimidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube
  • 12
  • [ 188057-49-0 ]
  • (E)-N'-(6-(2,4-dichlorophenyl)-2-cyanofuro[3,2-b]pyridin-3-yl)-N,N-dimethylformimidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube
  • 13
  • [ 188057-49-0 ]
  • (E)-N'-(6-(benzo[d][1,3]dioxol-5-yl)-2-cyanofuro[3,2-b]pyridin-3-yl)-N,N-dimethylformimidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Inert atmosphere; Microwave irradiation 5: neat (no solvent) / 0.43 h / 90 °C / Inert atmosphere; Microwave irradiation
Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube
  • 14
  • [ 188057-49-0 ]
  • 7-phenylpyrido[2',3':4,5]furo[3,2-d]pyrimidin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube 6: neat (no solvent) / 0.5 h / 170 °C / Inert atmosphere; Microwave irradiation; Sealed tube
  • 15
  • [ 188057-49-0 ]
  • 7-(4-methylphenyl)pyrido[2',3':4,5]furo[3,2-d]pyrimidin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube 6: neat (no solvent) / 0.5 h / 170 °C / Inert atmosphere; Microwave irradiation; Sealed tube
  • 16
  • [ 188057-49-0 ]
  • 7-(4-methoxyphenyl)pyrido[2',3':4,5]furo[3,2-d]pyrimidin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube 6: neat (no solvent) / 0.5 h / 170 °C / Inert atmosphere; Microwave irradiation; Sealed tube
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