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CAS No. : | 381233-75-6 | MDL No. : | MFCD08688586 |
Formula : | C5H3BrINO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WAUPPDAXWKLNNU-UHFFFAOYSA-N |
M.W : | 299.89 | Pubchem ID : | 12027787 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 47.48 |
TPSA : | 32.86 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) : | -7.22 cm/s |
Log Po/w (iLOGP) : | 1.66 |
Log Po/w (XLOGP3) : | 1.28 |
Log Po/w (WLOGP) : | 1.74 |
Log Po/w (MLOGP) : | 1.97 |
Log Po/w (SILICOS-IT) : | 3.22 |
Consensus Log Po/w : | 1.97 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.0 |
Solubility : | 0.301 mg/ml ; 0.001 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.57 |
Solubility : | 8.08 mg/ml ; 0.0269 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.72 |
Solubility : | 0.0567 mg/ml ; 0.000189 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.14 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.6% | With N-iodo-succinimide In acetonitrile at 82℃; for 0.333333 h; | Will contain 5-bromo-2-hydroxypyridine (2.5 g, 14.4 mmol), A mixture of iodosuccinimide (4.7 g, 20.9 mmol) and acetonitrile (40 mL) was stirred at 82 ° C for 20 min. After cooling to room temperature, filtration, the cake was recrystallized from ethyl acetate to give 5-bromo-2-hydroxy-3-iodopyridine (65) (4.0 g). The yield was 92.6percent. |
83% | With N-iodo-succinimide In acetonitrile for 4 h; Reflux | To 5-bromo-2-hydroxypyridine I (5g, 29mmol) was added solid N Jodosuccinimide (7.lg, 32mmol) in acetonitrile (l2OmL). The solution was stirred at reflux for 4 hours and followed by TLC. The solution was cooled to room temperature, filteredand washed with methanol. 5-bromo-2-hydroxy-3-.iodopyridine 2 was obtained as a pink solid (yield: 83percent). |
33% | With N-iodo-succinimide In N,N-dimethyl-formamide at 50℃; for 6 h; | Synthesis of 5-bromo-3-iodopyridin-2-ol (218): 5-Bromopyridin-2-ol (1.74 g, 10 mmol) was dissolved in DMF (40 mL) and NIS (2.7 g, 12 mmol) was added at room temperature. The reaction mixture was heated at 50 °C for 6 h. The reaction mixture was cooled down to room temperature, poured into 50 mL of water, extracted with EtOAc (60 mL X 3). The combined organic layers were washed with brine, dried over anhydrous Na2S04, and concentrated under reduced pressure to give 5-bromo-3-iodopyridin-2-ol (218) as yellow solid (1.0 g, 33percent yield). LCMS: m/z 301.9 [M+H]+; tR = 1.34 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With N-iodo-succinimide In toluene at 90℃; for 0.333333 h; Inert atmosphere | To a solution of 5-bromo-2-(1H)-pyridone (18.8 gf 10.8 mmol) in dry toluene {400 ml_) was added N-iodosuccinimide (24.3 g, 10.8 mmol) under nitrogen. The reaction mixture was stirred at 90 °C for 20 minutes then cooled to 25 °C. The precipitate was filtered off and washed with methanol, dried under vacuum to give the pink-orange color solid 28.0 g (86percent). 1H NMR (300 MHz, CDCi3 ) δ 8.1 (s, 1 H), 7.6 (s, 1 H). Mass caicuiated for formula C5H3BrINO 298.84, observe MS ES+: 300.0/302.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | at 160℃; for 4 h; | 2 (9g, 3Ommol) was dissolved in phenyiphosphonic dichloride 90percent (l0OmL,0.3mol). The mixture was stirred and heated (160°C) for 4 hours and followed by TLC. At room temperature, it was introduced drops in a vial of 1 L filled with water and cooled at 0°C. The solution was neutralized by addition of NH4OH solution. The mixture wasextracted in ethyl acetate. The product was obtained as a white solid, 5-bromo-2-chloro-3- iodopyridine 3 (yield: 82percent), |
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