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CAS No. : | 443-87-8 | MDL No. : | MFCD03788546 |
Formula : | C7H7FO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OMGVVVBQKWNRQA-UHFFFAOYSA-N |
M.W : | 126.13 | Pubchem ID : | 302628 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 33.39 |
TPSA : | 20.23 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.63 cm/s |
Log Po/w (iLOGP) : | 1.68 |
Log Po/w (XLOGP3) : | 2.03 |
Log Po/w (WLOGP) : | 2.26 |
Log Po/w (MLOGP) : | 2.24 |
Log Po/w (SILICOS-IT) : | 2.25 |
Consensus Log Po/w : | 2.09 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.39 |
Solubility : | 0.509 mg/ml ; 0.00403 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.08 |
Solubility : | 1.04 mg/ml ; 0.00827 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.45 |
Solubility : | 0.451 mg/ml ; 0.00357 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
With pyridine; at 0℃; for 2h; | 18.6 g (147 mmol) of <strong>[443-87-8]3-fluoro-2-methylphenol</strong> (Lock et al. Chem. Ber. 1936, 69, 2253-55) in 150 ml of dichloromethane and 16.6 ml of pyridine are admixed dropwise at 0 C. with 13.5 ml (155 mmol) of propionyl chloride. The mixture is stirred for two hours and 100 ml of 2 M hydrochloric acid are added. The mixture is extracted with dichloromethane and washed with water. Drying over sodium sulphate and removal of the solvent in vacuo give 20.6 g of 3-fluoro-2-methylphenyl propionate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With caesium carbonate; In acetonitrile; for 24h;Heating / reflux; | EXAMPLES 113 TO 124 A mixture of the appropriate phenol [commercial, unless stated below, (1 eq)], caesium carbonate (4 eq) and either the product of preparation 4 (1 eq) or preparation 6 (1 eq) in acetonitrile (2 mL) was heated under an atmoshphere of nitrogen, at reflux for 24 hours. The crude mixture then was partitioned between dichloromethane and water and passed through a phase separation tube. The organic solution was concentrated in vacuo and the residue was purified by HPLC using a Phenomenex Luna C18 column, eluting with water/0.1% formic acid:acetonitrile/0.1% formic acid, 95:5 to 5:95, to afford the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 38 Preparation of 3-fluoro-2-methylphenol 4h 0.65 g (3.69 mmol) of epoxide 2l (a mixture of 2l, 2l', 2l" above) in solution in 3 cm3 of anhydrous DMF were heated to reflux for 3 h; 91% of transposition ketone 6b was then detected by macrobore GC (verification by mass/GC coupling). 0.86 g (2 eq.) of DMAP were then added and the mixture was again heated to reflux for 3 h. It was acidified (pH=1) with 3N HCl, extracted with ether, concentrated, and a 3N sodium hydroxide solution was added to the ether phase (while the mixture was kept stirred for 5 to 10 min), the ether phase was removed and the material was washed once with ether. The aqueous phase was acidified using a solution with 3N HCl (pH=1) and was extracted with ether (4*15 cm3), dried over MgSO4, filtered and evaporated down. The crude product obtained was purified by flash chromatography on silica (eluent: ether/petroleum ether=5/95). 0.10 g of phenol 4h were obtained (macrobore GC purity>97%). The yield of compound 4h was 22%. MW: 126.132 1 H NMR: 7.15-6.30 (m, 3H); 5.15 (s, 1H mobile); 2.14 (d, 3H, J=2 Hz). IR in cm-1: nuOH =345c(broad); nuC=C =1620 (weak), 1595. MS (m/e): 126 (M+, 100); 125 (87); 109 (10.5); 108 (28); 107 (14.5); 97 (30.5); 95 (10); 77 (16.5); 49 (21). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With ammonium formate;palladium 10% on activated carbon; In ethanol; at 90℃; for 3h; | Step 9B Palladium on carbon (10 wt. %, 50% wet, 7.5 g, 3.5 mmol) was added to benzyl ether 9a (12.2 g, 57 mmol) and ammonium formate (16.0 g, 250 mmol) in ethanol (150 mL). The mixture was stirred at 90 C. for 3 h, cooled to ambient temperature, filtered through celite and concentrated in vacuo. The residue was purified by silica gel chromatography eluding with 0 to 10% ethyl acetate in hexanes to afford 9-1 as a colorless oil (5.6 g, 79%). 1H NMR (300 MHz, CDCl3) delta 7.00 (m, 1H), 6.61 (m, 2H), 5.11 (br s, 1H), 2.16 (d, J=2.1 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Step 12B To phenol 9-1 (4.5 g, 34 mmol) in N,N-dimethylacetamide (40 mL) under a nitrogen atmosphere was added potassium t-butoxide (4.2 g, 37 mmol) and the mixture was stirred for 15 min to obtain an almost homogeneous solution. In a separate flask zinc dichloride (4.3 mL, 1M in diethylether, 4.3 mmol) was added to epoxide 12a (chiral) in N,N-dimethylacetamide (60 mL). To this mixture was added the phenoxide solution and the resultant mixture was stirred at 80 C. for 17 h. Aqueous 10% sodium hydroxide (50 mL) was added and stirring was continued at 80 C. for a further 1 h. The mixture was cooled to ambient temperature and partitioned between de-ionized water (150 mL) and ethyl acetate (300 mL). The aqueous layer was extracted with ethyl acetate (4*100 mL) and the combined organics were washed with saturated aqueous sodium chloride (3*100 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue contained a large amount of N,N-dimethylacetamide and was dissolved in ethyl acetate (400 mL) and extracted with de-ionized water (4*100 mL). The organic layer was washed with saturated aqueous sodium chloride (200 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography eluding with 0 to 25% ethyl acetate in hexanes to afford 12b as a white solid (3.0 g, 60%). 1H NMR (300 MHz, CDCl3) delta 7.22-7.32 (m, 2H), 7.11-7.21 (m, 3H), 7.07 (d, J=8.4 Hz, 1H), 6.75 (t, J=8.7 Hz, 1H), 5.77 (s, 1H), 4.09 (dd, J=11.4 and 3.6 Hz, 1H), 3.69 (dd, J=11.4 and 7.5 Hz, 1H), 3.19 (d, J=16.2 Hz, 1H), 3.10 (s, 1H), 3.08 (d, J=16.2 Hz, 1H), 2.15 (dd, J=7.5 and 3.6 Hz, 1H), 2.07 (d, J=2.4 Hz, 1H). APCI MS m/e: 271.0 ([M+H-H2O]+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.85 g | With 4-dimethylaminomethyl-pyridine; triethylamine; In dichloromethane; at 20℃; | A solution of commercially available <strong>[443-87-8]3-fluoro-2-methylphenol</strong> 2.0 g, 15.9 mmol) and tert-butylchlorodimethylsilane (3.6 g, 23.8 mmol) in dichloromethane (20 mL) was prepared at room temperature. Triethylamine (5.5 mL, 39.6 mmol) and 4-dimethylaminomethylpyridine (0.1 g, 0.8 mmol) were added and stirring was continued overnight at room temperature. The mixture was diluted with ethyl acetate (200 mL) and washed with water (3 x 30 mL), brine, then dried over sodium sulfate, filtered and concentrated by rotary evaporation to furnish the product Intermediate-29 as a colorless oil (3.85 g, 101% yield). -NMR (500 MHz, CDC13) delta 6.77 (q, 1H), 6.43 (t, 1H), 6.36 (d, 1H), 1.90 (d, 3H), 0.80 (s, 9H), 0.00 (s, 6H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
<strong>[443-87-8]3-fluoro-2-methylphenol</strong> (34 mg, 0.27 mmol) was dissolved in 5 mL of tetrahydrofuran, followed by addition of sodium hydride (13 mg, 0.33 mmol). After stirring for 2 hours, the reaction solution was added with (S)-1-(2-fluoro-4-iodophenyl)-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-8-methyl-2,4 ,7-trioxo-pyrido[2,3-d]pyrimidin-5-yl trifluoromethanesulfonate 28d (150 mg, 0.22 mmol), then warmed up to 60C and stirred for 1 hour. The reaction solution was concentrated under reduced pressure to obtain the crude title compound (S)-5-(3-fluoro-2-methylphenoxy)-1-(2-fluoro-4-iodophenyl)-3-((2,2-dimethyl-1,3-diox olan-4-yl)methyl)-8-methylpyrido[2,3-d]pyrimidine-2,4,7(1H,3H,8H)-trione 28e (145 mg, pale yellow liquid), which was used directly in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
<strong>[443-87-8]3-fluoro-2-methylphenol</strong> (30 mg, 0.24 mmol) was dissolved in 5 mL of tetrahydrofuran, followed by addition of sodium hydride (12 mg, 0.30 mmol). After stirring for 2 hours, the reaction solution was added with 1-(2-fluoro-4-iodophenyl)-3-(4-methoxybenzyl)-8-methyl-2,4,7-trioxo-pyrido[2,3-d]pyr imidin-5-yl trifluoromethanesulfonate 1j (136 mg, 0.20 mmol), warmed up to 60C and stirred for 1 hour. The reaction solution was concentrated under reduced pressure to obtain the title compound 5-(3-fluoro-2-methylphenoxy)-1-(2-fluoro-4-iodophenyl)-3-(4-methoxybenzyl)-8-methylpyrido[2,3-d]pyrimidine-2,4,7(1H,3H,8H)-trione 1k (131 mg, pale yellow liquid), which was used directly in the next step without further purification. MS m/z (ESI): 658.1 [M+1] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
<strong>[443-87-8]3-fluoro-2-methylphenol</strong> (34 mg, 0.27 mmol) was dissolved in 5 mL of tetrahydrofuran, followed by addition of sodium hydride (13 mg, 0.33 mmol). After stirring for 2 hours, the reaction solution was added with (R)-5-(3-fluoro-2-methylphenoxy)-1-(2-fluoro-4-iodophenyl)-3-((2,2-dimethyl-1,3-diox olan-4-yl)methyl)-8-methylpyrido[2,3-d]pyrimidine-2,4,7(1H,3H,8H)-trione 27d (150 mg, 0.22 mmol), and stirred for 12 hours. The reaction solution was concentrated under reduced pressure to obtain the crude title compound (R)-5-(3-fluoro-2-methylphenoxy)-1-(2-fluoro-4-iodophenyl)-3-((2,2-dimethyl-1,3-diox olan-4-yl)methyl)-8-methylpyrido[2,3-d]pyrimidine-2,4,7(1H,3H,8H)-trione 27e (145 mg, pale yellow liquid), which was used directly in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With potassium carbonate; potassium iodide; In acetone; at 80℃; for 16h; | To a solution of <strong>[443-87-8]3-fluoro-2-methylphenol</strong> (25 g, 198.40 mmol) in acetone (500 mL) were added chloroacetone (37.70 g, 396.8 mmol), K2C03 (136.89 g, 992 mmol) and catalytic amount of Kl (3.29 g, 19.84 mmol) at room temperature. The reaction mixture was stirred at 80 C for 16 h. The mixture was allowed to room temperature, filtered and the filtrate was concentrated under reduced pressure. The crude compound was purified by flash chromatography using 2% ethyl acetate in petroleum ether as an eluent to afford intermediate B (12 g, 33%) as a thick liquid. 1H NMR (300 MHz, CDCI3): delta 7.08 (q, J = 8.1 Hz, 1 H), 6.71 (t, J = 8.4 Hz, 1 H), 6.46 (d, J = 8.7 Hz, 1 H), 4.53 (s, 2H), 2.31 (s, 3H), 2.21 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | To a solution of <strong>[443-87-8]2-methyl-3-fluorophenol</strong> (5 g, 39.64 mmol) in DMF (60 ml), was added potassium carbonate (6.03 g, 43.61 mmol). After 10 minutes of stirring at room temperature, methyl-4-bromobutyrate (8.31 g, 43.61 mmol) was added. The white suspension was heated at 50C for 24 hours. After cooling to room temperature, MeOH (50 ml), water (50 ml) and sodium hydroxide 32% (30 ml) were added. The reaction mixture was heated at 80C for 30 minutes. After cooling to room temperature, ice (100 g) was added, then HCI 5N was added to pH 3. The solid was filtered, washed with water (3x50 ml) and dried by heating under reduced pressure over P205. To the obtained white powder, polyphosphoric acid (PPA, 100 g) was added, then the mixture was heated at 90C for 15 minutes. Ice (300 g) was slowly added and the precipitate was filtered, and dried under reduced pressure over P205 to give 6.64 g (86%) of 8-fluoro-9-methyl-3,4- dihydrobenzo[b]oxepin-5(2H)-one as a yellow solid. LC/MS (m/z, MH+): 195 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
143 mg | With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 80℃; for 3h;Inert atmosphere; | 1- [2-(Dodecylsulfonyl)pyrimidin-5-ylj -5 ,6-dihydropyrimidine-2,4( 1 H,3H)-dione (500 mg), <strong>[443-87-8]3-fluoro-2-methylphenol</strong> (193 mg) and K2C03 (244 mg) were suspended in DMF (7 mL), stirred at room temperature under a nitrogen atmosphere, and then stirred for 3 hours at 80C. Water was added to the reaction solution, and the resulting solid was washed with water to obtain the object compound (143 mg).NMR2: 2.12(3H, d, J=1.8Hz), 2.90(2H, t, J=6.7Hz), 3.89(2H, t, J=6.7Hz), 6.93(1H, d, J=8.2Hz), 6.95-7.03(1H, m), 7.18-7.27(1H, m), 7.61(1H, brs), 8.55(2H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; sodium carbonate; In dimethyl sulfoxide; at 90℃; for 72h; | A mixture of 4-nitrophenyl (R)-4-(1 -(5-chlorothiophene-2- carboxamido)ethyl)piperidine-1 -carboxylate (100 mg, 0.228 mmol), 3-fluoro-2- methylphenol (288 mg, 2.28 mmol), Na2C03(48 mg, 0.46 mmol), DMAP (4.8 mg, 0.039 mmol) and DMSO (2 ml_) was heated to 90C for 3 days. The reaction mixture was partitioned between EtOAc/H20, and the layers were separated. The organic layer was washed with brine and dried over Na2S04. Solvent was removed under vacuum and the residue was purified by Gilson (C18, 50-100% MeCN in water with 0.1 % formic acid) to afford the title compound as a white solid.1H NMR (400 MHz, DMSO) delta 8.32 (d, J = 7.7 Hz, 1 H), 7.71 (d, J = 4.0 Hz, 1 H), 7.30 - 7.15 (m, 2H), 7.06 (t, J = 8.7 Hz, 1 H), 6.94 (d, J = 8.1 Hz, 1 H), 4.27 - 4.14 (m, 1 H), 4.10 - 3.98 (m, 1 H), 3.91 - 3.79 (m, 1 H), 3.09 - 2.94 (m, 1 H), 2.90 - 2.75 (m, 1 H), 2.02 (s, 3H), 1 .84 - 1 .71 (m, 2H), 1 .70 - 1 .61 (m, 1 H), 1 .31 - 1 .16 (m, 2H), 1 .15 (d, J = 6.7 Hz, 3H). LCMS (ESI) m/z calcd for C20H22CIFN2O3S: 424.10. Found: 425.32/427.25 (M/M+2)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With caesium carbonate; In dimethyl sulfoxide; at 140℃; for 1h;Microwave irradiation; | A mixture of 4-nitrophenyl (R)-4-(4-(benzyloxy)-1 -(4- fluorobenzamido)butyl)piperidine-1 -carboxylate (400 mg, 0.73 mmol), 3-fluoro-2- methylphenol (367 mg, 2.91 mmol), Cs2C03(948 mg, 2.91 mmol) and DMSO (6 mL) was heated to 140C by microwave. After stirred at this temperature for 1 h, the reaction mixture was partitioned between EtOAc/H20, and the layers were separated. The organic layer was washed with brine and dried over Na2S04. Solvent was removed under vacuum and the residue was purified by chromatography on silica gel to afford the title compound (310 mg, 79%). LCMS (ESI) m/z calcd for C31H34F2N2O4: 536.25. Found: 537.41 (M+1)+. |
Tags: 443-87-8 synthesis path| 443-87-8 SDS| 443-87-8 COA| 443-87-8 purity| 443-87-8 application| 443-87-8 NMR| 443-87-8 COA| 443-87-8 structure
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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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