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CAS No. : | 4470-83-1 | MDL No. : | MFCD00832077 |
Formula : | C9H5Cl2N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VAXOCTXTVIVOQE-UHFFFAOYSA-N |
M.W : | 198.05 | Pubchem ID : | 676553 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 51.76 |
TPSA : | 12.89 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) : | -4.82 cm/s |
Log Po/w (iLOGP) : | 2.23 |
Log Po/w (XLOGP3) : | 3.78 |
Log Po/w (WLOGP) : | 3.54 |
Log Po/w (MLOGP) : | 2.98 |
Log Po/w (SILICOS-IT) : | 3.72 |
Consensus Log Po/w : | 3.25 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.07 |
Solubility : | 0.017 mg/ml ; 0.0000859 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.74 |
Solubility : | 0.0357 mg/ml ; 0.00018 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.94 |
Solubility : | 0.00229 mg/ml ; 0.0000116 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 1.6 |
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 |
---|---|---|
75% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 25℃; for 6 h; Inert atmosphere | General procedure: PdCl2(dppf), PdCl2(tbpf) and (A.caPhos)PdCl2. A mixture of the halogenated heterocycle (0.66 mmol) in anhydrous THF (13.2 mL) was degassed by bubbling argon for few minutes. Then, PdCl2(dppf) (27.0 mg, 0.033 mmol, 5.0 molpercent), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and finally NaBH4 (42.4 mg, 1.12 mmol, 1.7 equiv) were introduced in sequence. The mixture was stirred at room temperature under argon for the proper time and then worked up as described above. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With potassium tert-butylate;palladium diacetate; (R)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; In 1,2-dimethoxyethane; at 80℃; for 18h; | To a degassed solution of <strong>[4470-83-1]2,8-dichloro-quinoline</strong> (3.00 g, 15.15 mmol, 1.0 equiv; commercially available) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (3.64 g, 18.18 mmol, 1.2 equiv; commercially available) in toluene (35 mL) was added KOtert-Bu (2.38 g, 21.21 mmol, 1.4 equiv), rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene (0.38 g, 0.61 mmol, 0.04 equiv) and tris(dibenzylideneacetone)-dipalladium(0) (0.31 g, 0.30 mmol, 0.02 equiv). The reaction mixture was stirred at 80 C. for 18 h, concentrated by evaporation under reduced pressure and the residue purified by silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane (+1% triethylamine)/ethyl acetate providing 1.73 g (31%) of the title compound. 1H NMR (300 MHz, CDCl3): delta1.37-1.51 (m, 2H), 1.48 (s, 9H), 2.17-2.22 (m, 2H), 2.96-3.04 (m, 2H), 4.07-4.17 (m, 3H), 4.76 (d, J=7.0 Hz, 1H), 6.64 (d, J=8.9 Hz, 1H), 7.11 (t, J=7.8 Hz, 1H), 7.49 (d, J=7.8 Hz, 1H), 7.64 (d, J=7.8 Hz, 1H), 7.80 (d, J=8.9 Hz, 1H). MS (ISP): 362.5 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
trifluoroacetic acid; In methanol; at 160℃; for 1.33333h;Microwave; | 4-Aminoimidazole-5-carboxamide HC1 salt (100 mg) and <strong>[4470-83-1]2,8-dichloroquinoline</strong>(100 mg) were dissolved in methanol (5 mL). Catalytic amount of TFA was added. Thereaction solution was microwaved at 160 C for 4800 s. The reaction solution wasevaporated and purified by flash column chromatography (CH2C12/MeOH = 20:1) togive 8-chloro-2-(5-carboxamide-lH-imidazol-4-ylamino)quinoline as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; at 100℃; for 72h; | 3-Amino-4-carboxamidepyrazole (100 mg) and <strong>[4470-83-1]2,8-dichloroquinoline</strong> (50 mg)were dissolved in methanol (5 mL). The reaction solution was heated at 100 C for 3 d.The reaction solution was evaporated. The residue was redissolved in methanol and ethylacetate, sonicated and cooled downed. The precipitation was filtered off, washed withdichloromethane to give 8-chloro-2-(4-carboxamide-lH-pyrazol-3-ylamino)quinoline as awhite solid. 1H NMR (DMSO-d6): 8 7.36 (br, 1H), 7.47 (t, 1H), 7.84 (br, 1H), 7.92 (m,2H), 8.28 (s, 1H), 8.47 (d, J= 9.0 Hz, 1H); LCMS: ret. time: 9.78 min.; purity: 95.89%;MS (m/e): 288.29 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34.5% | Step 1: Preparation of compound 175-2 [00618] To a solution of compound 175-1 (9.5 g, 0.048 mol) in THF (100 mL) was added LDA (2M, 29 mL, 0.058 mol) at -78 oC under N2. The reaction mixture was stirred for 1 h after addition. Then CH3CHO (2.5 g, 0.058 mol) was added to the above solution. The reaction mixture was stirred for 4 h at the same temperature. TLC showed the reaction was completed. The reaction mixture was poured into water (100 mL) and extracted with EtOAc (100 mL*3). The organic phase was evaporated under reduced pressure. The residue was purified by silica- gel column to provide compound 175-2 (4 g, 34.5%). | |
Example 25; 1-(2,8-Dichloroquinolin-3-yl)ethanol; To a cold solution of diisopropylamine (6.6 mL, 1.1 eq) in THF (100 mL) was added dropwise a solution of Bu11Li (1.1 eq, 2.5 M, 18.7 mL) in hexane at -20 0C. The resulted LDA solution was kept in 0 0C for 30 min and cooled to -78 0C before addition of a solution of <strong>[4470-83-1]2,8-dichloroquinoline</strong> (8.4 g, 42.4 mmol) in THF (44 mL) dropwise. The temperature was controlled below -72 0C by adjusting of adding rate (15 min). After 45 min, MeCHO (3.6 mL, 1.5 eq) was added dropwise. After 30 min, the reaction was quenched with NH4Cl and partitioned between EtOAc (150 mL) and water (100 mL). The combined organics were washed with water, brine, dried over Na2SO4. Removal of solvent gave colorless oil which was purified by column chromatography on silica gel (DCM/Hexane, 3/2) to give an oil. Hexane was added (80 mL) and the mixture was left over night. Filtration gave a white solid. 1H NMR (400 MHz, CDCl3) delta ppm 8.43 (s, IH), 7.84 (d, J=8.0 Hz, IH), 7.79 (d, J = 8.0 Hz, IH), 7.50 (t, J = 8.0 Hz, IH), 5.40 (q, J = 8.0 Hz, IH), 1.63 (d, J = 8.0 Hz, 3H). Mass Spectrum (ESI) m/e = 242 (M+l). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 2: Preparation of N-((8-Chloro-2-(2-chlorophenyl)quinolin-3-yl)- methyl)-9H-purin-6-amine; 2,8-DichIoroquinoline-3-carbaldehyde; A solution of LDA (14.8 mL 1.5M in cyclohexene, 22.2 mmol, 1.1 eq) in THF (30 mL) was stirred at -78 0C as a solution of <strong>[4470-83-1]2,8-dichloroquinoline</strong> (4.0 g, 20.2 mmol) in THF (15 mL) was added dropwise. The mixture stirred for two hours, at which time a solution of ethylformate (6.5 mL, 80.8 mmol, 4 eq) in THF (10 mL) was added slowly, and the mixture continued to stir at -78 0C for four hours. Wet THF (1 mL H2O in 5 mL THF) was added to quench the reaction and it was warmed to room temperature. After partitioning between Et2O and water, the aqueous layer was further extracted with Et2O, and the combined organic layers <n="48"/>were dried over MgSO4, filtered and condensed under reduced pressure. The residue was chromatographed on a silica column using a 0-50 % gradient of EtOAc in hexane. 2,3-Dichloroquinoline-3-cataubaldehyde was obtained as a yellow solid. IH NMR (400 MHz, DMSO-d6) delta ppm 10.25 (1 H, s), 8.93 (1 H, s), 8.14 (1 H, d, J=8.6 Hz)5 8.03 (1 H, d, J=9.0 Hz), 7.55 - 7.64 (1 H, t, J=8.0 Hz) Mass Spectrum (ESI) m/e = 226.0 and 227.9 (M+l) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene;palladium diacetate; In tert-butyl alcohol; | Example 1: compound (51) of table IAccording to route (A), a mixture of <strong>[4470-83-1]2,8-dichloroquinoline</strong> (98.5mg) and 2-amino-4,6-dimethylpyridine (67.1mg), Pd(OAc)2 (2.2mg), XantPhos (5.8mg) and Cs2CO3 (456mg) in 2mL of t-BuOH gave compound (51) (99.7mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In ethanol; at 120℃; for 1.3h; | A solution of 3-pyrrolidin-3-yl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (0.020 g, 0.000046 mol, prepared as in Example 15, Steps 1-3, omitting the chiral separation performed in Step 2) and <strong>[4470-83-1]2,8-dichloroquinoline</strong> (0.020 g, 0.00010 mol) in ethanol (0.020 mL, 0.00034 mol) and N,N-diisopropylethylamine (20.0 microL, 0.000115 mol) was heated at 120 C. for 1.3 h. The crude was purified by LCMS (C18 column eluting with a gradient ACN/H2O containing 0.15% NH4OH at 5 mL/min) to give 16 mg. LCMS (M+1): 599. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With caesium carbonate;palladium diacetate; In tert-butyl alcohol; | A reaction mixture of <strong>[4470-83-1]2,8-dichloroquinoline</strong> (101 mg, 0.5 mmol, 1 eq.) and 4-methoxy-3-(2-morpholinoethoxy)aniline (143 mg, 0.55 mmol, 1.1 eq.), Pd(OAc)2 (2.3 mg, 2 mol%), XantPhos (6 mg, 2 mol%) and Cs2CO3 (465 mg, 2.8 eq.)) in t-BuOH (2 mL) was heated at 90C and stirred for 20 hours. The reaction mixture was then concentrated under reduced pressure and the resulting residue was diluted with ethyl acetate. The organic phase was washed with water, dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel to give compound (23) (44 mg, 21 %). 1H NMR (300 MHz, CDCl3) delta 8.06 (d, J = 1.9, 1H), 7.85 (d, J = 8.9, 1H), 7.70 (dd, J = 1.2, 7.6, 1H), 7.53 (dd, J = 1.0, 7.9, 1H), 7.18 (t, J = 7.8, 1H), 6.99 (s, 1H), 6.93 (dd, J = 2.4, 8.6, 1H), 6.85 (dd, J = 2.9, 8.8, 2H), 4.29 (t, J = 6.1, 2H), 3.85 (s, 3H), 3.78 - 3.68 (m, 4H), 2.88 (t, J = 6.1, 2H), 2.66 - 2.52 (m, 4H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate;copper(I) oxide; 8-quinolinol; In dimethyl sulfoxide; at 170℃; for 1h;microwave irradiation; | A mixture of ethyl l-(5,6-dichloro-lH-benzo[ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; at 25℃; for 6h;Inert atmosphere; | General procedure: PdCl2(dppf), PdCl2(tbpf) and (A.caPhos)PdCl2. A mixture of the halogenated heterocycle (0.66 mmol) in anhydrous THF (13.2 mL) was degassed by bubbling argon for few minutes. Then, PdCl2(dppf) (27.0 mg, 0.033 mmol, 5.0 mol%), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and finally NaBH4 (42.4 mg, 1.12 mmol, 1.7 equiv) were introduced in sequence. The mixture was stirred at room temperature under argon for the proper time and then worked up as described above. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.3 g | With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In tert-butyl alcohol; at 90℃; for 20h;Inert atmosphere; | General procedure: According to route (A), the compound of formula (III) is placed in a protic solvent such as tert-butanol. The compound of formula (IV) is then added in a 1.1 molar ratio with respect to the compound of formula (III) in presence of CS2CO3, in a 2.8 molar ratio, in the presence of Xantphos (4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene), in a 2 mol% amount relative to the total amount of compound of formula (III), and in the presence of Pd(OAc)2, in a 2 mol% amount relative to the total amount of compound of formula (III). The reaction mixture is then heated at 90C, and stirred during 20 hours, under argon. The reaction mixture is concentrated under reduced pressure and the resulting residue is diluted with ethyl acetate. The organic phase is then washed twice with water,dried on magnesium sulphate, filtered and concentrated under reduced pressure. The residue could then be purified by column chromatography on silica gel to yield pure compounds (6), (43), (77), (80), (90), (112) and (136). According to route (A), a mixture of <strong>[4470-83-1]2,8-dichloroquinoline</strong> (1.5g) and 2-amino- 4methylpyridine (904mg), Pd(OAc)2 (34mg), XantPhos (88mg) and Cs2C03 (7.0g) in 30mL of t-BuOH gave compound (6) (1.3g). NMR (300 MHz, DMSO) delta 10.23 (s, 1H), 8.96 (s, 1H), 8.18 (d, J = 8.8, 2H), 7.78 (dd, J = 7.7, 13.7, 2H), 7.46 (d, J = 8.9, 1H), 7.31 (t, J = 7.8, 1H), 6.86 (d, J = 4.3, 1H), 2.37 (s, 3H). 1 C NMR (75 MHz, DMSO) delta 153.63, 153.61, 148.37, 147.32, 142.65, 137.52, 129.68, 129.47, 126.82, 125.06, 123.26, 118.36, 115.10, 113.31, 21.24. MS (ESI) [M+H]+= 270 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In neat (no solvent); at 75℃; for 0.166667h; | A solution 1.00g (.005mol) <strong>[4470-83-1]2,8-dichloroquinoline</strong> and .70g(.006mol) 2-thiophenethiol was stirred and heated at 75oC for 10min. After cooling, the mixture was diluted with 20mL ethyl acetate. The organic layer was washed three times with equal portions of 5% sodium sulfite, then once with an equal portion of 10% sodium hydroxide, dried with magnesium sulfate and allowed to evaporate. 1.00g of solid 2 were obtained which required no further purification (72% yield). mp: semi solid at room temp. 1H NMR (400MHz, CDCl3) 7.94 (d, 1H), 7.78 (d, 1H), 7.65 (m, 2H), 7.45 (d, 1H), 7.35 (t, 1H), 7.20 (m, 1H), 7.08 (d, 1H). 13C NMR (400MHz, CDCl3) 119.2, 126.5, 127.0, 127.6, 127.6, 127.7, 128.9, 129.5, 130.5, 137.5, 137.6, 144.3, 164.3. IR (NaCl) 3400, 3000, 1100, 903. Anal. calc. 276.97 m/z ASAP (- mode) 275.97 (C13H8ClNS2) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In tert-butyl alcohol; at 120℃; for 1.16667h;Microwave irradiation; | A reaction mixture of <strong>[4470-83-1]2,8-dichloroquinoline</strong> (198 mg, 1.0 mmol, 1 eq.), 5- bromo-4-(tri fluoromethyl )pyri din-2 -amine (241 mg, 1.0 mmol, 1 eq.), Pd(OAc)2 (4.5 mg, 0.02 mmol, 2 mol%), XantPhos (11.6 mg, 0.02 mmol, 2 mol%) and Cs2C03 (782 mg, 2.4 mmoles, 2.4 eq.) in /-BuOH (4 mL) was heated in a microwave reactor at 120C for 70 minutes. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure and the resulting residue was diluted with ethyl acetate. The organic phase was then washed with water, dried over MgS04, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel to afford N-[5-bromo-4-(trifluorornethyl)pyridin-2-yl]-8-chloroquinolin-2-arnine (21) (300 mg, 75%). H NMR (300 MHz, CDC13) 8 9.71 (s, 1H), 8.51 (s, 1 H), 8.06 (d, J = 9.0 Hz, 1H), 7.81 (m, 2H), 7.65 (d, J = 7.8 Hz, HI), 7.33 (t, J = 7.8 Hz, 1 H), 7.00 (d, J = 9.0 Hz, 1 H). MS (ESI) [M+H]+ - 403.7 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With copper(l) iodide; caesium carbonate; In N,N-dimethyl-formamide; at 150℃; for 0.833333h;Microwave irradiation; | Example 5: 8-chloro-2-((4-(trifluoromethyl)pyridin-2-yl)oxy)quinoline ; compound (46) A reaction mixture of 2,8-dichloroquinolrne (79 mg, 0.4 rnmol, 1 eq.), 2- hydroxy-4-(trifluoromethyl)pyridine (65 mg, 0.4 mmol, 1 eq.), Cul (76 mg, 0.4 mmol, 1 eq.) and CS2CO3 (391 mg, 1.2 mmol, 3 eq.) in DMF (6 mL) was heated in a microwave reactor at 150C for 50 minutes. Upon cooling to room temperature, water was added to the reaction mixture. The undissolved solids were filtered through celite and the resulting filtrate was twice extracted with ethyl acetate. The organic phase was washed with water and a saturated aqueous solution of brine, dried over MgSO-i, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel to afford 8-chloro-2- [4-(trifluoromethyl)pyridin-2-yl]oxy}quinoline (46) (68 mg, 52%). 1H NMR (300 MHz, CDCI3) delta 8.40 (d, J = 7.2 Hz, 1 H), 8.34 (d, J = 8.8 Hz, 1H), 8.18 (d, J= 8.8 Hz, 1H), 7.90 (d, J= 7.2 Hz, 1H), 7.85 (d FontWeight="Bold" FontSize="10" J= 7.9 Hz, 1H), 7.56 (t, J= 7.9 Hz, 1H), 6.98 (s, 1H), 6.53 (d, J= 7.9 Hz, 1H). I3C NMR (75 MHz, CDC13) 6 161.6, 151.2, 143.4, 142.3, 138.7, 138.2, 137.4, 133.4, 130.6, 129.1, 127.6, 126.7, 120.2, 119.7, 102.3. MS (ESI) [M+Hf = 325.1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With copper(l) iodide; caesium carbonate; In N,N-dimethyl-formamide; at 150℃; for 0.833333h;Microwave irradiation; | Example 6: 8-chloro-2-(^(trifluoromethoxv)phenoxvkiuinoline ; compound (48) A reaction mixture of 2,8 -dichloroquinoline (2x 79 mg, 2x 0.4 mmol, 1 eq.), 4- (trifluoromethoxy)phenol (2x 52 ^uL, 2x 0.4 mmol, 1 eq.), Cul (2x 76 mg, 2x 0.4 mmol, I eq.) and Cs2C03 (2x 391 mg, 2x 1.2 mmol, 3 eq.) in DMF (2x 6 mL) was heated in a microwave reactor at 150 C for 50 minutes. Upon cooling to room temperature, water was added to the reaction mixture. The undissolved solids were filtered through celite and the resulting filtrate was twice extracted with ethyl acetate. The organic phase was washed with water and a saturated aqueous solution of brine, dried over MgS(, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel to afford 8-chloro-2-[4-(trifluoromethoxy)phenoxy]quinoline 48 (212 mg, 78%). NMR (300 MHz, CDC13) delta 8.12 (d, J = 8.8 Hz, I H), 7.73 (d, J = 8.1 Hz, 1 H), 7.66 (d, J = 8.1 Hz, 1H), 7.46 (d, J = 9.1 Hz, 2H), 7.38 - 7.22 (m, 3H), 7.12 (d, J = 8.8 Hz, 1H). 13C NMR (75 MHz, CDC13) delta 161.5, 151.9, 145.9, 142.7, 140.5, 132.0, 130.3, 127.0, 126.4, 125.1, 122.8, 122.2, 119.0 (t, J = 255 Hz), 1 13.6. MS (ESI) [M+H]+ = 340.1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; at 110℃; for 12h;Inert atmosphere; | General procedure: A mixture of the 2-chloroquinoline or the 2-chloropyridine (1equiv), substituted thiophenol (1.2equiv), K2CO3 (1.5equiv), and DMF (0.5M) was heated to 110C under N2 for 12h. The resulting mixture was diluted with EtOAc and filtered. The filtrate was washed with H2O three times, and then the organic layer was purified through column chromatography. The resulting product (1equiv) was dissolved in DCM (0.1M), and then meta-chloroperoxybenzoic acid (2.1equiv, 70%) was added at 0C under N2 and the mixture was stirred at room temperature for additional 12h. The reaction mixture was washed with cold 2N NaOH solution three times, and then the organic layer was collected and evaporated to provide the product. |
Yield | Reaction Conditions | Operation in experiment |
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95% | In isopropyl alcohol; at 90℃; | 3. Preparation of (8-chloro-quinolin-2-yl)-(4-trifluoromethoxyphenyl)-amine (free base) without a Palladium-Catalyst 2,8-Dichloroquinoline (125 g; 0.63 mol) was slurried in 4-(trifluoromethoxy)aniline (280 g; 1 .58 mol) and isopropanol (240 ml_) and the mixture was heated to 90C. The mixture was stirred for 3-4 h when HPLC indicated complete conversion of dichloroquinoline. Thereafter, additional isopropanol (730 ml_) was added and the mixture cooled to approx. 40C. Water (2.5 L) was added slowly and the resulting precipitate was collected by suction filtration. The filter cake was dried under reduced pressure and afterwards recrystallized from boiling cyclohexane (1 .5 L) in order to yield pure product as an off-white solid. Yield: 203 g (95%) Chemical purity: 99.9% (peak area at lambda=254 nm). The identity of (8-chloro-quinolin-2-yl)-(4-trifluoromethoxyphenyl)-amine was verified by 1 H-NMR (Fig. 1 ); FT-IR (Fig. 2) and GC-MS (Fig. 3). The NMR spectrum was characterized by the following signals: 1 H NMR (400 MHz, CDCI3) delta ppm 6.87 (m, 2 H); 7.23 (m, 3 H); 7.55 (dd, J=8.01 , 1 .28 Hz, 1 H); 7.72 (dd, J=7.52, 1 .28 Hz, 1 H); 7.90 (m, 3 H). The IR-spectrum was characterized by the following signals: 3406; 1626; 1606; 1535; 1506; 1475; 1425; 1392; 1257; 1217; 1 146; 1001 ; 849; 822; 795; 754; 719; 673; 663; 631 cm"1. The solid state characteristics were investigated by means of DSC and XRPD and is as follows: The DSC thermogram (Fig. 4) is characterized by a single endotherm with an onset temperature of 120C (± 2C) and a peak temperature of 121 (± 2C). A characteristic x-ray powder diffractogrann is given in Fig. 5 and its characteristic signals are summarized in the following table: Major peaks can be seen at angles 7.3, 14.6 and 18.3 with relative intensities of 100.0%, 86.4% and 18.3%, respectively. Further prominent peaks can be seen at angles 23.0 and 24.8 with relative intensities of 18.1 % and 35.1 %, respectively. Additional prominent peaks can be seen at angles 28.3 and 29.5 with relative intensities of 13.8% and 1 1 .2%. Finally, remarkable peaks can be seen at angles 18.6, 22.3, 24.1 , 29.0 and 42.6 with relative intensities of 8.2%, 8.0%, 7.1 %, 8.6% and 7.4%, respectively. |
54% | General procedure: A mixture of substrate 2 (0.5 mmol), 1 (0.6 mmol), Pd(OAc)2 (2 mol%), Xphos (4 mol%), NaOtBu (2.0 equiv.) and Na2SO4 (2.0 g) were added to the 25 mL screw-capped stainless-steel vessel, along with two stainless steel balls ( = 1.4 cm). After that, the vessel was placed in the mixer mill, and the contents were ball milled at 30 Hz for 60 min. At the end of the reaction, small portion (3 mL) ethyl acetate and (3 mL) H2O were added in to the vessel and grinding for another 2 min at 30 Hz. Then, after the washing by brine, the organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue, which was purified by flash column chromatography on silica gel to give the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Ca. 60%; Ca. 27% | With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In tert-butyl alcohol; at 90℃; for 20h;Inert atmosphere; | 2. Preparation of (8-chloro-quinolin-2-yl)-(4-trifluoromethoxyphenyl)-amine (Comperative Example) 2,8-Dichloroquinoline (984mg) is placed in 20 ml tert-butanol. 4- (trifluoromethoxy)aniline (743 muIota_) is then added in presence of 4.6g Cs2CO3, in the presence of 58mg Xantphos (4,5-Bis(diphenylphosphino)-9,9- dimethylxanthene), and in the presence of 22mg Pd(OAc)2. The reaction mixture is then heated at 90C and stirred during 20 hours under argon. The reaction mixture is concentrated under reduced pressure and the resulting residue is diluted with ethyl acetate. The organic phase is then washed twice with water, dried on magnesium sulphate, filtered and concentrated under reduced pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | All the ligands and the corresponding complexes were synthesized in the similar manner; a typical synthesis of complex 3a is described as follows: in a 100mL flask, pyrazole (0.69g 10.09mmol) was dissolved in 50mL of DMF, and NaH (0.29g, 12.16mmol) was added to the solution, the reaction mixture was stirred for 30min. 2,8-Dichloroquinoline (2.0g, 10.09mmol) was then slowly added to the flask, after the reaction mixture was refluxed for 48h under a nitrogen atmosphere, the reaction was terminated with ice water after cooling to room temperature, and a white suspension was formed. The precipitate was filtered and recrystallized from ethanol, and dried under vacuum at 30C to give the desired product 1a as a white solid. Yield, 1.6g (69.0%). 1H NMR (400MHz, CDCl3, delta, ppm): 8.91 (d, 1H, qun-H), 8.28 (t, 2H, pyz-H), 7.80 (m, 3H, qun-H), 7.42 (t, 1H, qun-H), 6.54 (s, 1H, pyz-H). 13C NMR (100MHz, CDCl3, delta, ppm): 142.8, 139.5, 130.5, 127.9, 126.7, 125.8, 113.1, 108.6. FT-IR (KBr; cm-1): 2924, 1612, 1600, 1503, 1419, 1394, 1043, 942, 835, 760, 668, 607. Anal. calc. for C12H9ClN3 (229.6): C, 62.76; H, 3.51; N, 18.30. Found: C, 63.20; H, 3.94; N, 17.88. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: All the ligands and the corresponding complexes were synthesized in the similar manner; a typical synthesis of complex 3a is described as follows: in a 100mL flask, pyrazole (0.69g 10.09mmol) was dissolved in 50mL of DMF, and NaH (0.29g, 12.16mmol) was added to the solution, the reaction mixture was stirred for 30min. 2,8-Dichloroquinoline (2.0g, 10.09mmol) was then slowly added to the flask, after the reaction mixture was refluxed for 48h under a nitrogen atmosphere, the reaction was terminated with ice water after cooling to room temperature, and a white suspension was formed. The precipitate was filtered and recrystallized from ethanol, and dried under vacuum at 30C to give the desired product 1a as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: All the ligands and the corresponding complexes were synthesized in the similar manner; a typical synthesis of complex 3a is described as follows: in a 100mL flask, pyrazole (0.69g 10.09mmol) was dissolved in 50mL of DMF, and NaH (0.29g, 12.16mmol) was added to the solution, the reaction mixture was stirred for 30min. 2,8-Dichloroquinoline (2.0g, 10.09mmol) was then slowly added to the flask, after the reaction mixture was refluxed for 48h under a nitrogen atmosphere, the reaction was terminated with ice water after cooling to room temperature, and a white suspension was formed. The precipitate was filtered and recrystallized from ethanol, and dried under vacuum at 30C to give the desired product 1a as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: All the ligands and the corresponding complexes were synthesized in the similar manner; a typical synthesis of complex 3a is described as follows: in a 100mL flask, pyrazole (0.69g 10.09mmol) was dissolved in 50mL of DMF, and NaH (0.29g, 12.16mmol) was added to the solution, the reaction mixture was stirred for 30min. 2,8-Dichloroquinoline (2.0g, 10.09mmol) was then slowly added to the flask, after the reaction mixture was refluxed for 48h under a nitrogen atmosphere, the reaction was terminated with ice water after cooling to room temperature, and a white suspension was formed. The precipitate was filtered and recrystallized from ethanol, and dried under vacuum at 30C to give the desired product 1a as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: All the ligands and the corresponding complexes were synthesized in the similar manner; a typical synthesis of complex 3a is described as follows: in a 100mL flask, pyrazole (0.69g 10.09mmol) was dissolved in 50mL of DMF, and NaH (0.29g, 12.16mmol) was added to the solution, the reaction mixture was stirred for 30min. 2,8-Dichloroquinoline (2.0g, 10.09mmol) was then slowly added to the flask, after the reaction mixture was refluxed for 48h under a nitrogen atmosphere, the reaction was terminated with ice water after cooling to room temperature, and a white suspension was formed. The precipitate was filtered and recrystallized from ethanol, and dried under vacuum at 30C to give the desired product 1a as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | General procedure: A mixture of substrate 2 (0.5 mmol), 1 (0.6 mmol), Pd(OAc)2 (2 mol%), Xphos (4 mol%), NaOtBu (2.0 equiv.) and Na2SO4 (2.0 g) were added to the 25 mL screw-capped stainless-steel vessel, along with two stainless steel balls ( = 1.4 cm). After that, the vessel was placed in the mixer mill, and the contents were ball milled at 30 Hz for 60 min. At the end of the reaction, small portion (3 mL) ethyl acetate and (3 mL) H2O were added in to the vessel and grinding for another 2 min at 30 Hz. Then, after the washing by brine, the organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue, which was purified by flash column chromatography on silica gel to give the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In tert-butyl alcohol; at 90℃; for 20h; | A reaction mixture of <strong>[4470-83-1]2,8-dichloroquinoline</strong> (101 mg, 0.5 mmol, 1 eq.) and 4-methoxy-3-(2-morpholinoethoxy)aniline(143 mg, 0.55 mmol, 1.1 eq.), Pd(OAc)2 (2.3 mg, 2 mol%), XantPhos (6 mg, 2 mol%) and Cs2CO3 (465 mg, 2.8eq.)) in t-BuOH (2 mL) was heated at 90C and stirred for 20 hours. The reaction mixture was then concentrated underreduced pressure and the resulting residue was diluted with ethyl acetate. The organic phase was washed with water,dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by columnchromatography on silica gel to give compound (23) (44 mg, 21%).1H NMR (300 MHz, CDCl3) delta 8.06 (d, J = 1.9, 1H), 7.85 (d, J = 8.9, 1H), 7.70 (dd, J = 1.2, 7.6, 1H), 7.53 (dd, J = 1.0,7.9, 1H), 7.18 (t, J = 7.8, 1H), 6.99 (s, 1H), 6.93 (dd, J = 2.4, 8.6, 1H), 6.85 (dd, J = 2.9, 8.8, 2H), 4.29 (t, J = 6.1, 2H),3.85 (s, 3H), 3.78 - 3.68 (m, 4H), 2.88 (t, J = 6.1, 2H), 2.66 - 2.52 (m, 4H)MS (ESI) [M+H]+ = 414.1 |
Tags: 4470-83-1 synthesis path| 4470-83-1 SDS| 4470-83-1 COA| 4470-83-1 purity| 4470-83-1 application| 4470-83-1 NMR| 4470-83-1 COA| 4470-83-1 structure
[ 815583-95-0 ]
2,8-Dichloro-4-methylquinoline
Similarity: 0.96
[ 815583-95-0 ]
2,8-Dichloro-4-methylquinoline
Similarity: 0.96
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