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CAS No. : | 76008-73-6 | MDL No. : | MFCD00013635 |
Formula : | C9H8BrClO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AMGWDYLEMSMUIO-UHFFFAOYSA-N |
M.W : | 263.52 | Pubchem ID : | 144749 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 55.24 |
TPSA : | 26.3 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) : | -5.17 cm/s |
Log Po/w (iLOGP) : | 2.35 |
Log Po/w (XLOGP3) : | 3.85 |
Log Po/w (WLOGP) : | 3.28 |
Log Po/w (MLOGP) : | 3.52 |
Log Po/w (SILICOS-IT) : | 3.36 |
Consensus Log Po/w : | 3.27 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.04 |
Solubility : | 0.0239 mg/ml ; 0.0000906 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.1 |
Solubility : | 0.021 mg/ml ; 0.0000797 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.35 |
Solubility : | 0.0118 mg/ml ; 0.0000448 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.91 |
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 |
---|---|---|
26% | With caesium carbonate; potassium nitrate; In sulfuric acid; N,N-dimethyl-formamide; | 4-(4-Bromo-2-ethoxycarbonyl-6-nitro-phenyl)-piperazine-1-carboxylic Acid tert-butyl Ester (20B): <strong>[76008-73-6]5-Bromo-2-chloro-benzoic acid ethyl ester</strong> (19.4 g, 73.8 mmol) was dissolved in 130 ml concentrated sulfuric acid and cooled to 0 C. To this solution, potassium nitrate (8.0 g, 79 mmol) was added as a solid. The reaction mixture was stirred at 0 C. for 1 hour, poured into ice, and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to an oil. This oil was dissolved in DMF and Boc-piperazine (10 g, 53.8 mmol) and cesium carbonate (20 g, 62 mmol) were added. The reaction mixture was heated to 70 C. for 2 hours, let cool to room temperature, diluted with ethyl acetate, and the organic layer washed with water, 10% citric acid, brine, dried over magnesium sulfate, filtered and concentrated to an oil. The product was purified by silica chromatography to give 4-(4-bromo-2-ethoxycarbonyl-6-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester, 6.5 g, 14.2 mmol, 26% yield. 1H NMR (500 MHz, CDCl3) 7.89 ppm (1H, s), 7.85 (1H, s), 4.45 ppm (2H, q), 3.51 ppm (4H, m), 3.06 ppm (4H, m) 1.51 ppm (9H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; In 2-Methylpentane; nitrogen; toluene; | a) 4-[4-Chloro-3-(ethoxycarbonyl)phenyl]hexahydro-1H-1,4-diazepine-1-carboxylic acid, 1,1-dimethylethyl ester A mixture of <strong>[76008-73-6]5-bromo-2-chloro-benzoic acid, ethyl ester</strong> (0.50 g), hexahydro-1H-1,4-diazepine-1-carboxylic acid, 1,1-dimethylethyl ester (0.46 g), cesium carbonate (0.86 g), palladium (II) acetate (8.5 mg) and (R)-BINAP (35 mg) in toluene (3 ml) was heated at 100 C. for 14 h in a pressure vessel flushed with nitrogen. The cooled reaction mixture was poured into water and extracted (3 times) with ethyl acetate. The combined organic extracts were washed with saturated sodium chloride solution and then dried over magnesium sulfate. Evaporation under reduced pressure gave an oil which was purified by chromatography over silica gel, eluding with 20% ethyl acetate in iso-hexane to yield the subtitle compound as an oil (0.21 g). MS (APCI+ve) 282/284 (M-BOC)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; In toluene; | a) (+/-)-2-Chloro-5-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-pyrrolidinyl]-benzoic acid, ethyl ester Prepared as described in Example 5a) using <strong>[76008-73-6]5-bromo-2-chloro-benzoic acid, ethyl ester</strong> (0.50 g), 3-pyrrolidinyl-carbamic acid 1,1-dimethylethyl ester (0.42 g), cesium carbonate (0.86 g), palladium (II) acetate (21 mg) and (R)-BINAP (88 mg) and toluene (3 ml) to afford the subtitle compound as an oil (0.25 g). MS (APCI+ve) 311/313 (M-BOC)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; In toluene; | a) 2-Chloro-5-[4-[[(1,1-dimethylethoxy)carbonyl]amino])-1-piperidinyl]-benzoic acid, ethyl ester Prepared as described in Example 5a) using <strong>[76008-73-6]5-bromo-2-chloro-benzoic acid, ethyl ester</strong> (0.50 g), 4-piperidinyl-carbamic acid, 1,1-dimethylethyl ester (0.46 g), cesium carbonate (0.86 g), palladium (II) acetate (8.5 mg) and (R)-BINAP (35 mg) and toluene (3 ml) to afford the subtitle compound as an oil (0.17 g). MS (APCI+ve) 383/385 (M+H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate;palladium diacetate; In toluene; | a) 4-(4-Chloro-3-ethoxycarbonyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester Piperazine-1-carboxylic acid tert-butyl ester (106 mg), <strong>[76008-73-6]3-bromo-6-chlorobenzoic acid ethyl ester</strong> (125 mg), cesium carbonate (220 mg), palladium acetate (5 mg) and R-BINAP (22 mg) were combined in toluene (2 ml) and heated at 100 C. in a sealed vessel for 48 hr. The cooled reaction was loaded onto a silica column and eluted with iso-hexane/ethyl acetate (4:1) to give the subtitle product (170 mg). MS (APCI+ve) 269/271 (M+H-(tert-butyloxycarbonyl))+ 1H NMR (CDCl3) delta7.28-7.31 (2H, m), 6.94 (1H, dd), 4.39 (2H, q), 3.58 (4H, t), 3.13 (4H, t), 1.48 (9H, s), 1.40 (3H, t). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35(z)Step 1. Under a nitrogen atmosphere, a 50 mL round bottom flask is charged with bis(pinacolato)diborane (1.16 g, 4.55 mmol), potassium acetate (1.11 g, 11.4 mmol) and 5-bromo-2- chloro-benzoic acid ethyl ester (1 g, 3.79 mmol). After bubbling nitrogen through the mixture for 5 minutes, dichloro[l,r-bis(diphenylphosphino)ferrocene]palladium DCM adduct [PdCl2(dppf), 93 mg, 0.11 mmol] is added. The resulting mixture is heated to 600C for 2 hours, cooled to room temperature and poured into EtOAc (50 mL). This mixture is washed with water, with brine, dried over sodium sulfate, filtered and concentrated to give 2-chloro-5-(4A5.5-tetramethyl-fl. 3.2]dioxaborolan-2-yl)- benzoic acid ethyl ester [LCMS: Rx = 5.1 minutes, MS: 311 (M+H)] and the dimerized side product, 4,3'-Dichloro-biphenyl-3,4'-dicarboxylic acid diethyl ester in 2:1 ratio (0.65 g total). The crude mixture is used for a next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 1 : (5-Bromo-2-chlorophenyPmethanolTo a solution of <strong>[76008-73-6]ethyl 5-bromo-2-chlorobenzoate</strong> (1 eq.) in THF (0.03 M) was added, at - 780C, DlBAL (2.5 eq). The reaction was stirred at -78C for 1 h and then warmed slowly to RT over 1 h. The reaction mixture was then diluted with ether and carefully quenched with aq. 6 M HCl. The organic layer was separated and the aqueous layer was back extracted with ether. The combined organic extracts were washed with sat. aq. NaHCO3 and brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded a white semi-solid. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 3: 1 (v/v) Hex : EtOAc) afforded the title compound as a light yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Ethyl 5-bromo-2-chlorobenzoate (100 g, 0.38 mol), dry benzene (450 mL), ethynyl(trimethyl)silane (44.7 g, 0.45 mol), piperidine (38.3 g, 0.45 mol) and tetra(triphenylphosphine)palladium (22.0 g, 0.019 mol) were placed under an atmosphere of Ar in a three-necked round-bottomed 1 liter flask, equipped with a magnetic stirrer and a thermometer. The mixture was stirred for 30 minutes and then cooled to 0 0C. Copper iodide (7.23 g, 0.038 mol) was added, and the obtained suspension was stirred for a further 2.5 hours at 30-35 0C and filtered. The separated precipitate was washed with benzene, and the combined filtrate was washed with saturated aqueous solutions of NH4CI and NaCI, dried over Na2SO4 <n="37"/>and evaporated. The crude product was purified by chromatography (hexane/ethylacetate 10:1) on a silica gel column to give ethyl 2-chloro-5-(2-(trimethylsilyl)ethynyl)benzoate in 95% (101 g) yield.A suspension of ethyl 2-chloro-5-(2-(trimethylsilyl)ethynyl)benzoate (101 g; 0.36 mol), mercury(2+) diacetate (8.6 g, 0.027 mol) in THF (250 mL) and concentrated H2SO4 (40 mL) was stirred at 600C for 3 hours. Then the mixture was cooled, diluted with ether (500 mL) and washed to obtain neutral medium. Then the solution was dried over Na2SO4 and evaporated. The residue was purified by chromatography (hexane/ethylacetate 4:1) on a silica gel column to give ethyl 5-acetyl-2-chlorobenzoate in 70% (57 g) yield.(Dimethoxymethyl)dimethylamine (40 mL) was added to a suspension of ethyl 5-acetyl-2- chlorobenzoate (57 g, 0.25 mol) in toluene (60 mL). The mixture was refluxed for 9 hours, during which time forming methanol was distilled off. The solution was then concentrated in vacuo, and the residue was purified by chromatography (ethyl acetate) on a silica gel column to afford ethyl 2-chloro-5-(3- (dimethylamino)acryloyl)benzoate as yellow prismatic crystals in 80% (57.6 g) yield.Hydrazine hydrate (5.5 g, 0.11 mol) was added to a suspension of ethyl 2-chloro-5-(3- (dimethylamino)acryloyl)benzoate (28 g, 0.1 mol) in ethanol (100 mL). The reaction mixture was left to stand at 20 0C overnight and then concentrated. The residue was purified by chromatography (ethylacetate/hexane 1 :2) on a silica gel column to afford ethyl 2-chloro-5-(1H-pyrazol-3-yl)benzoate in 94% (22.9 g) yield.A suspension of compound ethyl 2-chloro-5-(1H-pyrazol-3-yl)benzoate (22.9 g, 0.091 mol), sodium methylate (7.4 g, 0.14 mol) in ethanol (250 mL) was refluxed for 10 minutes. The formed precipitate was separated and dissolved in water (1 L). The obtained aqueous solution was acidified with concentrated HCI to pH about 2 that caused precipitation. The precipitate was separated by filtration, washed with water and dried to give 2-chloro-5-(1H-pyrazol-3-yl)benzoic acid as yellowish crystals in 92% (18.9 g) yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; at 60℃; for 2.08333h; | Under a nitrogen atmosphere, a 50 mL round bottom flask is charged with bis(pinacolato)diborane (1.16 g, 4.55 mmol), potassium acetate (1.11 g, 11.4 mmol) and 5-bromo-2- chloro-benzoic acid ethyl ester (1 g, 3.79 mmol). After bubbling nitrogen through the mixture for 5 minutes, dichloro[l,r-bis(diphenylphosphino)ferrocene]palladium DCM adduct [PdCl2(dppf), 93 mg, 0.11 mmol] is added. The resulting mixture is heated to 60C for 2 hours, cooled to room temperature and poured into EtOAc (50 mL). This mixture is washed with water, with brine, dried over sodium sulfate, filtered and concentrated to give 2-chloro-5-(4A5,5-tetramethyl-[l . 3,2"|dioxaborolan-2-yl)- benzoic acid ethyl ester [LCMS: Rtau = 5.1 minutes, MS: 311 (M+H)] and the dimerized side product, 4,3'-Dichloro-biphenyl-3,4'-dicarboxylic acid diethyl ester in 2:1 ratio (0.65 g total). The crude mixture is used for a next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With caesium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 110℃; for 2h; | Intermediate 9; <n="48"/>Ethyl 2-chloro-5-cyclopropylbenzoateIn a schlenck tube, a mixture of ethyl 5-bromo-2-chlorobenzoate (7.60 mmol, 2 g), 2- cyclopropyl-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (7.59 mmol, 1.3 g), Cs2CO3 (18.97 mmol, 6.18 g), PdCI2CIpPf-CH2CI2 (0.76 mmol, 0.620 g) in dioxane (70 ml) and water (15 ml) was heated for 2 hours at 11O0C1 under argon atmosphere. The solvent was evaporated and the mixture was extracted between ethyl acetate and water. The crude mixture was purified by chromatography over SiO2 eluting hexane/ethyl acetate mixtures and affording 1.5 g (yield 92%) of the expected product. 1H NMR (300 MHz, CDCI3) delta ppm: 0.67-0.71 (t, 3H), 0.97-1.01 (m, 2H), 1.38-1.43(t, 3H), 1.85-1.91 (m, 1 H), 4.36-4.43 (q, 2H), 7.07-7.10 (d, 1 H), 7.26-7.32 (m, 1H), 7.49 (s, 1 H). ESI/MS (m/e, %): 225 [(M+1)+, 100]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate;(bis(tricyclohexyl)phosphine)palladium(II) dichloride; In water; toluene; at 100℃; for 4h; | Intermediate 17: Ethyl 2-chloro-5-cyclopropylbenzoate; Ethyl 5-bromo-2-chlorobenzoate (5.0 g, 19.0 mmol), cyclopropyl boronic acid (2.12 g, 24.7 mmol), dichlorobis(tricyclohexylphosphine) palladium (II) (0.70 g, 0.95 mmol) and tripotassium phosphate (14.1 g, 66.4 mmol) was added to a degassed mixture of toluene (80 mL) and H2O (5 mL) and the suspension was heated at 100 0C for 4 hours. The <n="143"/>reaction mixture was concentrated in vacuo and the residue was purified by chromatography on silica gel eluting with EtOAc/isohexane (0 - 5%) to give the title compound as an oil (2.11 g): ^ NMR deltaO.l - 0.72 (2H, m), 0.91 - 1.01 (2H, m), 1.31 (3H, t), 1.94 - 2.03 (IH, m), 4.31 (2H, q), 7.21 - 7.25 (IH, m), 7.41 (IH, d), 7.47 (IH, d). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With caesium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; for 16h;Heating / reflux; | Method Q- Step a- [l,4]diazepane- l-carboxylic acid tert-butyl ester (1 1.5 g, 0.057 mmol), 5,bromo-2-chloro benzoic acid ethyl ester (12.5 g, 0.047 mmol), Pd(OAc)2 (0.21 g, 1 mmol), rac-2,2' bis(diphenylphosphino)- l , l '-binaphtyl (BINAP) (0.88 g, 1.4 mmol) and cesium carbonate (21.5 g, 66 mmol) were suspended in toluene (200 mL). Reaction was refluxed 16 h then cooled to 200C. The reaction mixture was poured into water (200 mL), and extracted with AcOEt (3 x 150 mL). The combined extracts were washed <n="69"/>with brine, dried over MgSO4 and concentrated under reduced pressure to give a brown oil that was purified by flash chromatography (eluent: n-hexane: AcOEt gradient from n-hexane:AcOEt 4: 1 to n-hexane:AcOEt 1 : 1) to afford 17.2 g of the title compound.(96%). 1H-NMR (400 MHz CDCl3): delta 1.37-1.48 (12H, m), 1.96-2.02 (2H, m),3.22-3.35 (2H, m), 3.50-3.64 (6H, m), 4.39 (2H, q), 6.76-6.78 (IH, m),7.10-7.1 1 (IH, m), 7.23-7.26 (IH, m). m/z 383 (M+H)+; retention time= 7.70. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 20 - 85℃; | Step a- Ethyl 5-bromo-2-chlorobenzoate (0.80 g, <n="28"/>3.04 mmol), rac-2,2'-bis(diphenylphosphino)-l,l '-binaphthyl (BINAP) (0.19 g, 0.30 mmol), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3) (0.28 g, 0.30 mmol) and cesium carbonate (Cs2CO3) (1.39 g, 4.26 mmol) were placed in a Schlenk tube and purged by repeated nitrogen/vacuum cycles for 30 minutes. Dry toluene (6 mL) and l-(2-dimethylaminoethyl) piperazine (0.55 mL, 3.65 mmol) were then added. The reaction mixture was stirred for 10 min at room temperature, heated at 85C overnight and then cooled to room temperature. The solution was diluted with EtOAc (30 mL), the insoluble material was filtered off and the filtrate was washed with saturated brine (15 mL). The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure to obtain a residue that was purified by flash chromatography (eluent gradient: EtOAc, EtOAc:MeOH/l : l, EtOAc:MeOH:NH3 in MeOH (2M)/1 : 1 :0.2) to afford 0.30 g of the title compound (30%). 1H-NMR (400 MHz, DMSO): delta 1.28 (3H, t), 2.12 (6H, s), 2.32-2.42 (4H, m), 2.47-2.51 (4H, m), 3.11-3.14 (4H, m), 4.27 (2H, q), 7.06-7.09 (IH, m), 7.18-7.19 (IH, m), 7.30-7.32 (IH, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 80℃; for 1h; | To a slurry of <strong>[76008-73-6]ethyl 5-bromo-2-chlorobenzoate</strong> (0.21 mL, 1.24 mmol), tetrakis(triphenylphosphine)palladium(0) (0.057 g, 0.050 mmol), ethylene glycol dimethyl ether (6.6 mL) and 2 N sodium carbonate (6 mL, 12 mmol) was added [6- (methyloxy)-2-naphthalenyl]boronic acid (0.3 g, 1.49 mmol) and the reaction mixture was heated at 80 0C for 1 h. The reaction mixture was cooled to room temperature and diluted with water, followed by ethyl acetate. The organic layer was separated, washed with water, followed by brine, dried over magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography over silica using a hexanes: ethyl acetate gradient of 0 to 30% ethyl acetate to afford 0.43 g (100%) of ethyl 2-chloro-5-[6-(methyloxy)-2-naphthalenyl]benzoate. 1H NMR (400 MHz, DMSO-J6): delta 8.21 (s, IH), 8.12 (d, J = 2 Hz, IH), 7.96 (dd, J = 8, 2 Hz, IH), 7.92 (s, IH), 7.90 (s, IH), 7.80 (d, J = 9 Hz, IH), 7.66 (d, J = 9 Hz, IH), 7.35 (d, J = 2 <n="172"/>Hz, IH), 7.19 (dd, J = 9, 2 Hz, IH), 4.35 (q, J = 7 Hz, 2H), 3.87 (s, 3H), 1.33 (t, J = 7 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 100℃; for 3h; | (Example 34) [3-(4-Chloro-4'-fluorobiphenyl-3-yl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepin-8-yl]methanol (Example Compound No. 1-127) (34a) Ethyl 4-chloro-4'-fluorobiphenyl-3-carboxylate ; To a solution of <strong>[76008-73-6]ethyl 5-bromo-2-chlorobenzoate</strong> (1.23 g, 4.7 mmol) in toluene (14 mL), ethanol (7 mL), and water (4 mL) were added (4-fluorophenyl)boronic acid (780 mg, 5.6 mmol), sodium carbonate (1.06 g, 10 mmol), and tetrakis(triphenylphosphine)palladium(0) (440 mg, 0.38 mmol), and the mixture was stirred at 100C for 3 h. The mixture was extracted with ethyl acetate, then washed with water, saturated aqueous sodium hydrogencarbonate, and saturated brine, and then dried with anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate = 4/1) to obtain the title compound as a colorless oily substance (515 mg, 39%). 1H NMR spectrum (400 MHz, CDCl3) deltappm: 1.43 (3H, t, J=7.0 Hz), 4.44 (2H, q, J=7.0 Hz) 7.15 (2H, t, J=8.6 Hz), 7.31-7.35 (1H, m), 7.47-7.58 (3H, m), 7.97 (1H, d, J=2.3 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10% | With potassium carbonate;molecular sieve; In toluene; | Example (Ia-1) N-[4-Chloro-3-(cyclopropylcarbamoyl)phenyl]-2-methyl-6-(pentafluoroethyl)-5-(trifluoromethyl)pyrimidine-4-carboxamide In a heat-dried flask, 975 mg (3.02 mmol) of 2-methyl-6-(pentafluoroethyl)-5-(trifluoromethyl)pyrimidine-4-carboxamide, 833 mg (6.03 mmol) of potassium carbonate, 287 mg (1.51 mmol) of copper iodide and molecular sieve are initially introduced under argon. Then, 795 mg (3.02 mmol) of <strong>[76008-73-6]ethyl 5-bromo-2-chlorobenzoate</strong>, 429 mg (3.02 mmol) of N,N'-dimethylcyclohexane-1.2-diamine and 5 ml of toluene are added dropwise. The reaction mixture is stirred at 100 C. in a microwave for 45 min and then diluted with ethyl acetate, filtered over Celite and concentrated by evaporation on a rotary evaporator. The residue is purified by means of flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1/5). This gives 0.16 g of ethyl 2-chloro-5-([2-methyl-6-(pentafluoroethyl)-5-(trifluoromethyl)pyrimidin-4-yl]-carbonyl}amino)benzoate (10%) as a beige solid. 1H-NMR (400 MHz, d6-DMSO): delta=8.05 (d, 1H), 7.81-7.78 (m, 1H), 7.59-7.52 (m, 1H), 4.36 (q, 2H), 2.88 (s, 3H), 1.33 (t, 3H) ppm. HPLC-MSa): log P=4.55; mass (m/z)=506 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | The required (2-chloro-5- ethylphenyl)methanol was prepared as follows: To a nitrogen purged solution of <strong>[76008-73-6]ethyl 5-bromo-2-chlorobenzoate</strong> (4.26 mL, 25.05 mmol) in THF (100 mL) was added lithium chloride (2.12 g, 50.09 mmol) and [1,1'- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.82 g, 1 mmol).Subsequently, the mixture was cooled to -78C, and a solution of diethylzinc (37.57 mL; 1 mol/1; 37.57 mmol) in heptane was added dropwise. The reaction mixture was allowed to come to RT overnight. The resulting reaction mixture was cooled to -10C and diluted with 300 mL Et20. Subsequently, a 1 M HC1 solution (150 mL) was added carefully. The organic layer was separated, dried (Na2S04), filtered, and concentrated in vacuo. The residue was purified by column chromatography (S1O2, Et20:hexanes 5:95) to afford ethyl 2-chloro-5- ethylbenzoate (4.61 g, 86%). To a nitrogen purged solution of ethyl 2-chloro5- ethyl-benzoate (1 g, 4.70 mmol) in THF (25 mL), cooled to -5C, was added diisobutylaluminiumhydride (14.11 mL; 14.11 mmol) in toluene. The reaction mixture was allowed to come to RT and stirred overnight. The resulting reaction mixture was cooled to -10C and and 5% aqueous NaHC03-solution (10 mL) was added. The organic layer was separated, dried (Na2S04), filtered, and concentrated in vacuo. The residue was purified by columnchromatography (S1O2, Et20:hexanes 1:3 followed by Et20:hexanes 1:1) to afford (2-chloro-6-ethylphenyl)methanol (0.59 g, 75%) which was used as such. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | The required (2-chloro-5- propylphenyl)methanol was prepared as follows: To a nitrogen purged solution of <strong>[76008-73-6]ethyl 5-bromo-2-chlorobenzoate</strong> (2 g, 7.59 mmol) in THF (14 mL) was added 0.5 M lithium chloride in THF (30 mL) and [1,1'- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.22 g, 0.3 mmol). Subsequently, the mixture was cooled to -78C, and a solution of N-propylzinc bromide (30.36 mL; 0.5 mol/l;15.18 mmol) was added dropwise. The reaction mixture was allowed to come to RT overnight. The resulting reaction mixture was cooled to -10C and diluted with 300 mL Et20. Subsequently, a 1 M HC1 solution (150 mL) was added carefully. The organic layer was separated, dried (Na2S04), filtered, and concentrated in vacuo. The residue was purified by column chromatography (S1O2, Et20:hexanes 5:95 followed by Et20:hexanes 1:0) to afford ethyl 2-chloro-5-propylbenzoate (1.1 g, 63%). To a nitrogen purged solution of ethyl 2-chloro-5-propyl-benzoate (1.12 g, 4.94 mmol) in THF (28 mL), cooled to -5C, was added diisobutylaluminiumhydride (14.82 mL; 14.82 mmol) in toluene. The reaction mixture was allowed to come to RT and stirred overnight. The resulting reaction mixture was cooled to -10C and and 5% aqueous NaHC03-solution (10 mL) was added. The organic layer was separated, dried (Na2S04), filtered, and concentrated in vacuo. The residue was purified by column chromatography (S1O2, Et20:hexanes 1:3 followed by Et20:hexanes 1:1) to afford (2-chloro-6-propylphenyl)methanol (0.76 g, 83%) which was used as such. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 16 1-{4-chloro-3-[(dimethyl)(4-ethyoxyphenyl)methyl]phenyl}-1-deoxy-beta-D-glucopyranose [Show Image] A. (5-bromo-2-chlorophenyl)(4-ethyoxyphenyl)(dimethyl)methane; 2.64 g of <strong>[76008-73-6]ethyl 5-bromo-2-chlorobenzoate</strong> and 10 ml of anhydrous THF were added into a 100-ml round-bottomed flask, and the resulting solution was cooled in ice water bath and magnetically stirred, and then 25 ml (1.0 M) of methyl iodine magnesium in THF was added using a pressure-equalizing funnel. After addition, the reaction mixture was stirred for one hour at room temperature, poured carefully into 200 ml of ice water, and adjusted to pH = 3-4 with concentrated hydrochloric acid. The resulting acidic mixture was extracted twice with 100 ml of dichloromethane. The combined extracts were washed with saturated NaCl solution, dried over anhydrous sodium sulfate, and evaporated to dryness on a rotary evaporator to give a colorless oily product, which was (5-bromo-2-chlorophenyl)dimethylmethanol. 1H NMR (DMSO-d6, 400 MHz), delta 7.95 (d, 1H, J = 2.8 Hz), 7.44 (dd, 1H, J = 2.6 Hz and 8.6 Hz), 7.3 (d, 1H, J = 8.0 Hz), 5.46 (s, 1H), 1.56 (s, 6H); ESI-MS, m/z = 249.2 ([M(79Br)+1]), 251.3 ([M(81Br)+1]). | ||
In tetrahydrofuran; at 20℃; for 1h;Cooling with ice; | A. (5-bromo-2-chlorophenyl)(4-ethyoxyphenyl)(dimethyl)methane[0097]2.64 g of <strong>[76008-73-6]ethyl 5-bromo-2-chlorobenzoate</strong> and 10 ml of anhydrous THF were added into a 100-ml round-bottomed flask, and the resulting solution was cooled in ice water bath and magnetically stirred, and then 25 ml (1.0 M) of methyl iodine magnesium in THF was added using a pressure-equalizing funnel. After addition, the reaction mixture was stirred for one hour at room temperature, poured carefully into 200 ml of ice water, and adjusted to pH=3-4 with concentrated hydrochloric acid. The resulting acidic mixture was extracted twice with 100 ml of dichloromethane. The combined extracts were washed with saturated NaCl solution, dried over anhydrous sodium sulfate, and evaporated to dryness on a rotary evaporator to give a colorless oily product, which was (5-bromo-2-chlorophenyl)dimethylmethanol. 1H NMR (DMSO-d6, 400 MHz), delta 7.95 (d, 1H, J=2.8 Hz), 7.44 (dd, 1H, J=2.6 Hz and 8.6 Hz), 7.33 (d, 1H, J=8.0 Hz), 5.46 (s, 1H), 1.56 (s, 6H); ESI-MS, m/z=249.2 ([M(79Br)+1]), 251.3 ([M(81Br)+1]). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid;Reflux; | General procedure: Intermediate 3: .0 To a mixture of commercially available 2-chloro-5-hydroxybenzoic acid (4 g, 23.18mmol) in dry EtOH ( 90 mL), concentrated sulphuric acid (1 mL, 17.62mmol) was added. The mixture was stirred under reflux overnight, then solvent evaporated under reduced pressure and the residue dissolved with DCM. A saturated solution of NaHCO3 was added, phases were separated, organics dried over sodium sulphate , filtered and evaporated to obtain 5 g of the corresponding 2-chloro-5-hydroxy- benzoic acid ethyl ester. HPLC-MS (Method 2): Rt = 1 .0 min MS: m/z = 201 .6 (M+H)+ | |
With sulfuric acid;Reflux; | General procedure: To a mixture of commercially available 2-chloro-5- hydroxybenzoic acid (4 g, 23.18 mmol) in dry EtOR (90 mE), concentrated sulphuric acid (1 mE, 17.62 mmol) was added. The mixture was stirred under reflux overnight, then solvent evaporated under reduced pressure and the residue dissolved with DCM. A saturated solution of NaHCO3 was added, phases were separated, organics dried over sodium sulphate, filtered and evaporated to obtain 5 g of the corresponding 2-chioro-5-hydroxybenzoic acid ethyl ester.10567] HPEC-MS (Method 2): R=1 .0 mm10568] MS: mlz=201.6 (M+H7 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.86 g | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; toluene; at 100℃; for 8h;Inert atmosphere; | Reference Example 3 2-Chloro-5-(cyclopropylethynyl)benzoic acid To a solution of <strong>[76008-73-6]ethyl 5-bromo-2-chlorobenzoate</strong>(1.9g) in DMF (12 mL), toluene (0.3 mL), cyclopropylacetylene (714 mg), copper iodide (275 mg), 24 dichloro bis(triphenylphosphine)palladium (1.01g) and triethylamine (20.1 mL) were added, and the mixture was degassed, stirred at 100C under argon atmosphere for 8 hours later, and then the reaction mixture was cooled to room temperature and diluted with ethyl acetate. The insoluble material was filtered off on celite. The mother liquor was washed with brine, dried over magnesium sulfate and concentrated. By purification on column chromatography, ethyl 2-chloro-5-(cyclopropylethynyl)benzoate (1.86g) was obtained as brown oil. This was dissolved in MeOH-THF (1:1, 60 mL), 10% aqueous sodium hydroxide solution (20 mL) was added, and the solution was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, water was added to the residue, and the mixture was separated with diethyl ether. The aqueous layer was separated, acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The residual solid was washed with n-hexane, and the titled compound (1.02g) was obtained as beige powder. |
1.86 g | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; toluene; at 100℃; for 8h;Inert atmosphere; | To a solution of <strong>[76008-73-6]ethyl 5-bromo-2-chlorobenzoate</strong>(1.9g) in DMF (12 mL), toluene (0.3 mL), cyclopropylacetylene (714 mg), copper iodide (275 mg), dichloro bis(triphenylphosphine)palladium (1.01g) and triethylamine (20.1 mL) were added, and the mixture was degassed, stirred at 100C under argon atmosphere for 8 hours later, and then the reaction mixture was cooled to room temperature and diluted with ethyl acetate. The insoluble material was filtered off on celite. The mother liquor was washed with brine, dried over magnesium sulfate and concentrated.By purification on column chromatography, ethyl 2-chloro-5-(cyclopropylethynyl)benzoate (1.86g) was obtained as brown oil.This was dissolved in MeOH-THF (1:1, 60 mL), 10% aqueous sodium hydroxide solution (20 mL) was added, and the solution was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, water was added to the residue, and the mixture was separated with diethyl ether. The aqueous layer was separated, acidified with 1N hydrochloric acid and extracted with ethylacetate.Theorganic layer was dried over magnesium sulfate and concentrated in vacuo. The residual solid was washed with nhexane,and the titled compound (1.02g) was obtained as beige powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With silica gel; In neat (no solvent); at 100℃; for 10h;Inert atmosphere; Sealed tube; | General procedure: These compounds were prepared using the same procedure as reported above, but at 100C for 6-28h. Following workup, the products (all solids) were recrystallized from EtOH to afford the isolated yields shown in Table 4. For analytical samples, purification was achieved by chromatography on a 15cm×2.5cm silica gel column eluted with 40-60% EtOAc in hexanes. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With silica gel; In neat (no solvent); at 100℃; for 12h;Inert atmosphere; Sealed tube; | General procedure: These compounds were prepared using the same procedure as reported above, but at 100C for 6-28h. Following workup, the products (all solids) were recrystallized from EtOH to afford the isolated yields shown in Table 4. For analytical samples, purification was achieved by chromatography on a 15cm×2.5cm silica gel column eluted with 40-60% EtOAc in hexanes. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With silica gel; In neat (no solvent); at 100℃; for 12h;Inert atmosphere; Sealed tube; | General procedure: These compounds were prepared using the same procedure as reported above, but at 100C for 6-28h. Following workup, the products (all solids) were recrystallized from EtOH to afford the isolated yields shown in Table 4. For analytical samples, purification was achieved by chromatography on a 15cm×2.5cm silica gel column eluted with 40-60% EtOAc in hexanes. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With silica gel; In neat (no solvent); at 100℃; for 16h;Inert atmosphere; Sealed tube; | General procedure: These compounds were prepared using the same procedure as reported above, but at 100C for 6-28h. Following workup, the products (all solids) were recrystallized from EtOH to afford the isolated yields shown in Table 4. For analytical samples, purification was achieved by chromatography on a 15cm×2.5cm silica gel column eluted with 40-60% EtOAc in hexanes. |
Tags: 76008-73-6 synthesis path| 76008-73-6 SDS| 76008-73-6 COA| 76008-73-6 purity| 76008-73-6 application| 76008-73-6 NMR| 76008-73-6 COA| 76008-73-6 structure
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