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CAS No. : | 1206972-45-3 | MDL No. : | MFCD18257007 |
Formula : | C6H3ClF3NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PONLSAHALFQCNY-UHFFFAOYSA-N |
M.W : | 197.54 | Pubchem ID : | 22000229 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 35.93 |
TPSA : | 22.12 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) : | -5.41 cm/s |
Log Po/w (iLOGP) : | 1.96 |
Log Po/w (XLOGP3) : | 2.95 |
Log Po/w (WLOGP) : | 3.89 |
Log Po/w (MLOGP) : | 1.25 |
Log Po/w (SILICOS-IT) : | 2.58 |
Consensus Log Po/w : | 2.53 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.16 |
Solubility : | 0.136 mg/ml ; 0.00069 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.08 |
Solubility : | 0.165 mg/ml ; 0.000838 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.27 |
Solubility : | 0.106 mg/ml ; 0.000535 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.99 |
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 |
---|---|---|
81% | With trimethylsilyl bromide In propiononitrile for 24 h; Reflux | 2-Bromo-5-trifluoromethoxy pyridine (31); A solution of 2-chloro-5-trifluoromethoxy pyridine (6, 7.0 g, 35.4 mmol) and bromotrimethylsilane (10.8 g, 9.3 mL, 70.8 mmol, 2 eq) in propionitrile (35 mL) was heated under reflux for 24 h. GC monitoring indicated 100percent conversion. The mixture was distilled in vacuum to afford pure 2-bromo-4-trifluoromethoxy pyridine (31, 7.0 g, 28.7 mmol, 81percent) as a colorless oil; b.p. 63-66 0C / 14 mbar. 1H NMR (CDCl3, 300 MHz): δ = 8.34 (d, J = 2.8 Hz, 1 H), 7.56 (d, J = 8.7 Hz, 1 H), 7.45 (dd, J = 8.7, 2.8 Hz, 1 H). - 19F NMR (CDCl3, 282 MHz): δ = -58.8. - 13C NMR (CDCl3, 75 MHz): δ = 145.6, 143.1, 139.2, 131.4, 129.0, 120.1 (q, J = 260 Hz). - C6H3BrF3NO (241): calcd. (percent) C 29.78, H 1.25, N 5.79; found C 29.96, H 1.41, N 5.64. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | at 120 - 150℃; | 2-Chloro-5-trifluoromethoxypyridine (6); 2-Chloro-5-trichloromethoxypyridine (5, 7.4 g, 30.0 mmol) is added dropwise to a molten mixture of SbF3 (10.7 g, 60.0 mmol, 2.0 eq) and SbCl5 (1.4 g, 0.6 mL, 4.6 mmol, 0.15 eq) at 120 0C and stirred for 3 h at 150 0C. GC monitoring indicates 100percent conversion and disappearance of byproduct OCF2Cl. The mixture is then cooled to 0 0C and dissolved in dichloromethane (100 mL). The solution is quenched with saturated aqueous solution of sodium hydrogencarbonate (100 mL) and potassium fluoride (20percent, 50 mL), the aqueous layer is extracted with dichloromethane (2 x 50 mL). The combined organic layers are dried over sodium sulfate and the solvent is distilled. The crude product is distilled under vacuum to afford pure 2-chloro-5-trifluoromethoxypyridine (6, 3.6 g, 18.0 mmol, 60percent) as a colorless oil; b.p. 41-43 °C / 20 mbar.1H NMR (CDCl3, 300 MHz): δ = 8.35 (s, 1 H), 7.55 (d, J = 8.7 Hz, 1 H), 7.41 (d, J= 8.7 Hz, 1 H). - 13C NMR (CDCl3, 75 MHz): δ = 149.3, 142.7, 140.1, 131.3, 125.1, 120.2 (q, J= 259 Hz). - MS(EI): m/z = 197 [M+], 162 [M+-Cl]. |
40% | at 120 - 175℃; for 18 h; | Step 1: (0630) To antimony trifluoride (4.05 g, 23 mmol) and antimony pentachloride (0.22 mL, 1.7 mmol) at 120° C. was added the trichloromethyl ether prepared in step 1 of scheme 25 (2.80 g, 11 mmol). The reaction was warmed to 165° C. under nitrogen and stirred for 14 h and then warmed to 175° C. and stirred for an additional 4 h. The reaction was cooled to room temperature. The resulting solid mass was stirred vigorously with saturated NaHCO3 (aq.) [Gas evolution] and EtOAc. The mixture was filtered through a plug of Celite washing with EtOAc. The filtrate was extracted with EtOAc. The combined organic layers were washed with water and brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-10percent EtOAc/hex over 30 minutes) (0.90 g, 40percent). |
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