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CAS No. : | 52570-33-9 | MDL No. : | MFCD12923250 |
Formula : | C9H9IO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IPPPZCXGKFWQEC-UHFFFAOYSA-N |
M.W : | 276.07 | Pubchem ID : | 15656853 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 55.4 |
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) : | -6.0 cm/s |
Log Po/w (iLOGP) : | 2.45 |
Log Po/w (XLOGP3) : | 2.79 |
Log Po/w (WLOGP) : | 2.39 |
Log Po/w (MLOGP) : | 3.11 |
Log Po/w (SILICOS-IT) : | 3.12 |
Consensus Log Po/w : | 2.77 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.55 |
Solubility : | 0.0783 mg/ml ; 0.000284 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.0 |
Solubility : | 0.277 mg/ml ; 0.001 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.81 |
Solubility : | 0.0428 mg/ml ; 0.000155 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.85 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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% | at 0℃; for 3 h; Heating / reflux | To a solution of compound 2 (63.0 g, 0.24 mol) in MeOH (300 mL) was added dropwise a freshly prepared solution of SOCI2 (52 mL, 0.72 mol) in MeOH (100 mL) at 0 0C. The mixture was heated to reflux for 3 hours. TLC (petroleum ether: ethyl acetate = 10:1) showed the reaction was complete, then the mixture was concentrated in vacuo. The residue was purified by column chromatography (petroleum ether) to afford compound 3 (60 g, 92percent) as brown oil. 1H NMR (400 MHz, CDCI3): δ 7.94-7.96 (d, J = 8.0 Hz, 1 H), 7.71-7.73 (d, J = 8.0 HzJ H), 6.87- 6.91 (t, J = 8.0 Hz, 1 H), 3.88 (s, 3H), 2.65 (s, 3H). |
87.5% | for 5 h; Heating / reflux | 3-Iodo-2-methylbenzoic acid (10.00 g, 38.16 mmol), methanol (50 ml) and concentrated sulfuric acid (0.6 ml, 11.45 mmol) were mixed, and the mixture was stirred for 5 hours while heating to reflux. The reaction solution was concentrated, ethyl acetate (80 ml) and water (30 ml) were added to the residue. The organic layer was separated and washed three times with a saturated aqueous sodium bicarbonate solution (30 ml) and once with 10percent brine (30 ml) . The organic layer was concentrated, to yield the title compound (9.22 g) (yield 87.5percent) .1H-NMR (CDCl3, TMS, 300 MHz) δ (ppm) : 2.67 (3H, s) , 3.90 (3H, s), 6.92 (IH, t, J = 7.8 Hz), 7.74 (IH, dd, J = 1.2 Hz, 7.8 Hz) , 7.98 (IH, dd, J = 1.2 Hz, 7.9 Hz) . |
80.4% | at 0 - 80℃; for 16 h; | [0469] To a solution of 3-iodo-2-methylbenzoic acid (2.0 g, 3.82 mmol) in dry MeOH (10 mL) at 0 °C was added thionyl chloride (681mg, 5.72 mmol). Then the reaction was heated to 80 °C for 16 hrs. TLC showed the starting material was consumed and one main spot was present. The reaction was cooled to rt and the solvent was removed. The residue was diluted with water (20 mL) and extracted with EA (40 mL) twice. The combined organic layers were washed with saturated sodium bicarbonate aqueous (30 mL), brine, dried over sodium sulfate, filtered and concentrated providing crude product, which was purified by column chromatography on silica-gel elution with petroleum ether:EA (from 0percent to 8percent) providing methyl 3-iodo-2-methylbenzoate (1.7 g, 80.4percent yield) as a colorless oil. MS (ESI) m/z 277.0 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.97 (dd, J = 1.2, 8.0 Hz, 1 H), 7.73 (dd, J = 0.8, 8.0 Hz, 1 H), 6.92 (t, J = 8.0 Hz, 1 H), 3.89 (s, 3 H), 2.66 (s, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In benzene; for 6h;Reflux; | To a solution of SM2-079 (4.00 g, 14.49 mmol) in benzene (66 mL) (CAUTION) at room temperature were added N- bromosuccinimide (NBS) (3.09 g, 17.39 mmol) and AIBN (237.9 mg, 1.45 mmol). The reaction was refluxed for 6 h, the mixture was cooled to rrom temperature and the solid obtained was filtered. The filtrate was diluted with EtOAc and washed with sat. NaHC03 solution, brine, dried (MgS04) and concentrated. The residue was purified by S1O2 chromatography with EtOAc/hexane (0% to 10% EtOAc, gradient elution) to obtain the title compound6 (4.95 g, 96%) as a white solid. NMR (500 MHz, DMSO- e) d 8.15 (dd, J = 1.3, 7.9 Hz, 1H), 7.85 (dd, J = 1.4, 7.8 Hz, 1H), 7.21 (t, J = 7.8 Hz, 1H), 5.03 (s, 2H), 3.88 (s, 3H). |
76% | With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 90℃; | To a solution of <strong>[52570-33-9]methyl <strong>[52570-33-9]3-iodo-2-methylbenzoate</strong></strong> (10.0 g, 36.2 mmol) in carbon tetrachloride (200 mL) was added BS (8.4 g, 47.1 mmol) and benzoyl peroxide (4.4 g, 18.1 mmol), the suspension was heated at 90 C overnight. The mixture was then cooled to RT and filtered. The filtrate was concentrated to give the crude product, which was purified by silica-gel column (light petro 100%) to give methyl 2-(bromomethyl)-3- iodobenzoate (9.8 g, 76%) as a yellow solid. |
47.5% | [0491] To a solution of <strong>[52570-33-9]methyl <strong>[52570-33-9]3-iodo-2-methylbenzoate</strong></strong> (2.0 g, 7.25 mmol) in CCl4 (50 mL) at rt was added N-bromosuccinimide (NBS) (1.42 g, 7.97 mmol). The reaction was heated to 85C for 5 minutes and AIBN (623 mg, 3.63 mmol) was added. The reaction was stirred at 85C for 16 hrs. cooled to rt, and the solid was filtered off. The filtrate was concentrated providing the crude product, which was purified by silica gel column chromatography with EA / petroleum ether from 0% to 3% providing methyl 2- (bromomethyl)-3-iodobenzoate (1.22 g, 47.5% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 8.04 (dd, J = 1.6, 8.0 Hz1H), 7.89 (dd, J = 1.6, 8.0 Hz1H), 7.04(t, J = 8.0 Hz, 1H), 5.12 (s, 2H), 3.95 (s, 3H). |
40% | To a solution of <strong>[52570-33-9]methyl <strong>[52570-33-9]3-iodo-2-methylbenzoate</strong></strong> (5.20 g, 18.8 mmol) in CCI4 (90 mL) at RT was added N-bromosuccinimide (NBS) (4.02 g, 22.6 mmol) then the reaction flask was purged with N2. After the mixture was stirred at 85 C for 5 m, 2,2?-azobis(2- methylpropionitrile) (AIBN) (1.62 g, 9.42 mmol) was added. The mixture was stirred overnight at 85 C then concentrated. The residue was diluted with H2O and extracted with EtOAc. The organic phase was dried over Na2S04, filtered, and concentrated to give the crude product, which was purified using silica gel eluting with EtOAc in petroleum ether from 0% to 1% to afford methyl 2-(bromomethyl)-3-iodobenzoate (2.64 g, 40% yield) as a solid. | |
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 15h;Heating / reflux; | b. 3-Iodo-2-[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-benzoic acid methyl ester[0236] A mixture of <strong>[52570-33-9]3-iodo-2-methyl-benzoic acid methyl ester</strong> (75 mmol, 20.7 g), N- bromosuccinimide (76.6 mmol, 13.8 g), benzoyl peroxide (890 mg), and CCl4 (300 mL) was refluxed with stirring for 15 h. After cooling to ambient temperature the mixture was filtered and the filtrate was concentrated in vacuo to give the title compound as a tan oil. The oil (26.3 g) was dissolved in dry DMF (75 mL). NaI (22.4 g), K2CO3 (20.5 g), and (toluene-4- sulfonylamino)-acetic acid methyl ester (19 g) were added and the mixture was stirred at ambient temperature for 24 h before it was poured into water (900 mL). The mixture was extracted with ethyl acetate (2x250 mL). The combined organic phases were washed with a solution of sodium meta-bisulfte (20 g) in water (300 mL) and water (2x300 mL) before they were dried over MgSO4 and concentrated in vacuo to give the title compound as a dark gum (38.1 g). The crude product was used in the next step without further purification; MS-(+)-ion: M+23 = 539.9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 0.833333h;Product distribution / selectivity; | 3-Iodo-2-methylbenzoic acid (38.00 g, 145.01 mmol), tetrahydrofuran (114 ml) and N,N-dimethylformamide (0.56 ml, 7.25 mmol) were mixed, and oxalyl chloride (27.61 g, 217.52 mmol) was added dropwise to the mixture with ice cooling over about 15 minutes. The mixture was stirred for 1 hour with ice cooling, and the reaction solution was concentrated under reduced pressure. Separately, triethylamine (24.95 g, 246.52 mmol) and methanol (76 ml) were mixed, and a solution of the acid chloride prepared above in tetrahydrofuran (76 ml) was added dropwise thereto under ice cooling over about 20 minutes. After completion of the dropwise addition, the mixture was stirred at room temperature for 30 minutes. Ethyl acetate (570 ml) and water (190 ml) were added to the reaction solution. The organic layer was separated and washed twice with 10% brine (38 ml) . The organic layer was concentrated, to yield the title compound (40.58 g) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43.3% | With caesium carbonate;Catalyst obtained from palladium(II) acetate and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 100 - 105℃; for 7h;Product distribution / selectivity; | Process using Pd Catalyst Under a nitrogen atmosphere, palladium acetate (223 mg, 0.99 mmol) , 4, 5-bis (diphenylphosphino) -9, 9-dimethylxanthene (Xantphos) (575 mg, 0.99 mmol) and toluene (62 ml) were mixed, and the mixture was stirred at room temperature for 15 minutes. To this solution, 2-amino-3-bromo-5-methylpyridine (6.20 g, 33.15 mmol), <strong>[52570-33-9]methyl <strong>[52570-33-9]3-iodo-2-methylbenzoate</strong></strong> (9.15 g, 33.15 mmol) and cesium carbonate (15.12 g, 46.41 mmol) were added. The mixture was stirred at an internal temperature of 100 to 105C for 7 hours. The reaction solution was cooled to room temperature, and water (50 ml) and toluene (50 ml) were added thereto. The organic layer was separated and washed sequentially with water (40 ml) and 10% brine (40 ml) . Silica gel (6 g) was added to the organic layer, the mixture was filtered, and the filtrate was concentrated under reduced pressure. Ethyl acetate (0.5 ml) and n-hexane (6 ml) were added to the concentrate, and the mixture was stirred at room temperature for 30 minutes. The crystals were collected by filtration, washed with ethyl acetate/n-hexane (1/12, 5 ml), and dried under reduced pressure at 40C, to yield the title compound (4.81 g) (yield 43.3%). 1H-NMR (CDCl3, TMS, 300 MHz) delta (ppm) : 2.23 (3H, s) , 2.52 (3H, s), 3.91 (3H, s), 6.78 (IH, brs) , 7.27 (IH, t, J = 8.0 Hz), 7.57-7.62 (2H, m) , 7.95 (IH, d, J = 1.1 Hz), 8.10 (IH, dd, J = 1.0 Hz, 8.1 Hz) .High resolution mass spectrometry Theoretical value: 334.0317 [M+] Measured value: 334.0313 [M+]Melting point: 63.9 to 64.7C |
43% | With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; at 100℃;Inert atmosphere; | General procedure: Under N2 atmosphere, to a solution of palladium acetate (120 mg, 0.53 mmol, 5 mol %) and XANTPHOS (309 mg, 0.53 mmol, 5 mol %) in anisole (30 mL) was added 3-bromo-5-methyl-pyridin-2-ylamine (5) (2.0 g, 10.7 mmol, 1.0 equiv), aryl iodides (6) (10.7 mmol) and cesium carbonate (4.9 g, 15.0 mmol, 1.4 equiv), and the mixture was stirred at 130 C for 1-13 h. After cooling to room temperature, water (40 mL) was added to the mixture. The mixture was concentrated in vacuo and ethyl acetate (100 mL) was added to the residue. The organic layer was washed with water (20 mL) and concentrated in vacuo to give the crude product, which was purified by flash chromatography to give 7. |
16.1%Chromat. | With potassium carbonate;copper(l) iodide; ethanolamine; In methoxybenzene; at 20 - 130℃; for 8.16667h;Product distribution / selectivity; | Under a nitrogen atmosphere, 2-amino-3-bromo-5- <n="125"/>methylpyridine (2.00 g, 10.69 mmol) , methyl 3-iodo-2- methylbenzoate (2.95 g, 10.69 mmol) , copper (I) iodide (204 mg, 0.11 mmol), ethanol amine (131 mg, 0.22 mmol), potassium carbonate (2.22 g, 16.04 mmol), and anisole (30 ml) were mixed, and the mixture was stirred at room temperature for 10 minutes. The mixture was heated and stirred at 130C for 8 hours. The reaction solution was cooled to room temperature, and water (30 ml) was added thereto. The mixture was concentrated under reduced pressure. The concentrate was dissolved in ethyl acetate (50 ml), activated carbon Shirasagi A was added, and the mixture was filtered. Water (20 ml) was added to the filtrate. The organic layer was separated and washed with water (20 ml) . The organic layer was concentrated. The concentrate was subjected to silica gel column chromatography (silica gel 20 g, eluent: ethyl acetate :n-hexane = 1:20), and the effective fraction was concentrated. Ethyl acetate (0.2 ml) and n-hexane (5 ml) were added to the residue, and the mixture was stirred at room temperature for 30 minutes. Next, the crystals were collected by filtration, and dried at 50C under reduced pressure, to yield the title compound (1.13 g) . (HPLC area%: 83.4% (methyl 3- [ (3-iodo-5-methylpyridin-2- yl) amino] -2-methylbenzoate: 16.1%)) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine;copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 20℃; for 5h; | Reference Example 17 Methyl 2-methyl-3-trimethylsilylethynylbenzoate In 10 ml of tetrahydrofuran were suspended <strong>[52570-33-9]methyl <strong>[52570-33-9]3-iodo-2-methylbenzoate</strong></strong> (1.20 g, 4.35 mmol) and copper (I) iodide (0.21 g, 1.10 mmol), and then, triethylamine (3.0 ml, 21.5 mmol) and trimethylacetylene (1.5 ml, 10.8 mmol) were added to the suspension to form a uniform solution. Then, to the mixture was added tetrakistriphenylphosphinepalladium (0) (0.72 g, 0.62 mmol), and the mixture was stirred at room temperature for 5 hours under argon atmosphere. After completion of the reaction, water was added to the reaction mixture, the resulting mixture was extracted with ethyl acetate, and the organic layer was washed successively with a saturated aqueous ammonium chloride solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was concentrated and the resulting residue was applied to silica gel chromatography (eluent: hexane/ethyl acetate=99/1 (volume ratio)) to obtain 1.05 g of the desired compound as black brownish oily product. CI-MS(m/z); 247(M++1), EI-MS(m/z); 246(M+) 1H-NMR(delta, CDCl3); 0.27(s, 9H), 2.70(s, 3H), 3.89(s, 3H), 7.17(t, J=7.8 Hz, 1H), 7.58(dd, J=7.8, 1.5 Hz, 1H), 7.78(dd, J=7.8, 1.5 Hz, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
copper(l) iodide; In DMF (N,N-dimethyl-formamide); at 80℃; for 16.0h; | Reference Example 18 Methyl 2-methyl-3-trifluoromethylbenzoate In 5 ml of dimethylformamide were suspended <strong>[52570-33-9]methyl <strong>[52570-33-9]3-iodo-2-methylbenzoate</strong></strong> (0.80 g, 2.90 mmol) and copper (I) iodide (0.12 g, 0.63 mmol), and methyl fluorosulfonyl(difluoro)acetate (1.0 ml, 7.91 mmol) was added to the suspension and the mixture was stirred at 80 C. for 6 hours under argon atmosphere. After allowing to coll, copper (I) iodide (0.18 g, 0.95 mmol) and methyl fluorosulfonyl(difluoro)acetate (2.0 ml, 15.8 mmol) were further added to the mixture and stirred at 80 C. for 10 hours. After completion of the reaction, pentane was added to the reaction solution, and after removing the precipitates, the filtrate was washed twice with water and once with a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was concentrated to obtain 0.62 g of the desired compound as colorless transparent oily product. CI-MS(m/z); 219(M++1), EI-MS(m/z); 218(M+) 1H-NMR(delta, CDCl3); 2.64(s, 3H), 3.93(s, 3H), 7.34(dd, J=7.8, 8.1 Hz, 1H), 7.77(d, J=8.1 Hz, 1H), 7.91(d, J=7.8 Hz, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride; In tetrahydrofuran; for 3h;Heating / reflux; | A solution of compound 3 (60 g, 0.217 mol) and 1-vinyl-2-pyrrolidinone (26.5 g, 0.239 mol) in anhydrous THF (200 mL) was added slowly to a gently refluxing suspension of sodium hydride (12.2 g, 60% in mineral oil, 0.304 mol) in THF (100 mL). After the addition, the mixture was stirred at reflux for additional 3 hours. TLC (petroleum ether: ethyl acetate = 10:1) showed the reaction was complete. The mixture was cooled and the excess sodium hydride was EPO <DP n="110"/>quenched with saturated aqueous ammonium chloride. The mixture was concentrated in vacuo to remove THF. The residue was extracted with ethyl acetate (600 mLx2). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give crude product 4, which was used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With thionyl chloride; at 0℃; for 3h;Heating / reflux; | To a solution of compound 2 (63.0 g, 0.24 mol) in MeOH (300 mL) was added dropwise a freshly prepared solution of SOCI2 (52 mL, 0.72 mol) in MeOH (100 mL) at 0 0C. The mixture was heated to reflux for 3 hours. TLC (petroleum ether: ethyl acetate = 10:1) showed the reaction was complete, then the mixture was concentrated in vacuo. The residue was purified by column chromatography (petroleum ether) to afford compound 3 (60 g, 92%) as brown oil. 1H NMR (400 MHz, CDCI3): delta 7.94-7.96 (d, J = 8.0 Hz, 1 H), 7.71-7.73 (d, J = 8.0 HzJ H), 6.87- 6.91 (t, J = 8.0 Hz, 1 H), 3.88 (s, 3H), 2.65 (s, 3H). |
87.5% | With sulfuric acid; for 5h;Heating / reflux;Product distribution / selectivity; | 3-Iodo-2-methylbenzoic acid (10.00 g, 38.16 mmol), methanol (50 ml) and concentrated sulfuric acid (0.6 ml, 11.45 mmol) were mixed, and the mixture was stirred for 5 hours while heating to reflux. The reaction solution was concentrated, ethyl acetate (80 ml) and water (30 ml) were added to the residue. The organic layer was separated and washed three times with a saturated aqueous sodium bicarbonate solution (30 ml) and once with 10% brine (30 ml) . The organic layer was concentrated, to yield the title compound (9.22 g) (yield 87.5%) .1H-NMR (CDCl3, TMS, 300 MHz) delta (ppm) : 2.67 (3H, s) , 3.90 (3H, s), 6.92 (IH, t, J = 7.8 Hz), 7.74 (IH, dd, J = 1.2 Hz, 7.8 Hz) , 7.98 (IH, dd, J = 1.2 Hz, 7.9 Hz) . |
80.4% | With thionyl chloride; at 0 - 80℃; for 16h; | [0469] To a solution of 3-iodo-2-methylbenzoic acid (2.0 g, 3.82 mmol) in dry MeOH (10 mL) at 0 C was added thionyl chloride (681mg, 5.72 mmol). Then the reaction was heated to 80 C for 16 hrs. TLC showed the starting material was consumed and one main spot was present. The reaction was cooled to rt and the solvent was removed. The residue was diluted with water (20 mL) and extracted with EA (40 mL) twice. The combined organic layers were washed with saturated sodium bicarbonate aqueous (30 mL), brine, dried over sodium sulfate, filtered and concentrated providing crude product, which was purified by column chromatography on silica-gel elution with petroleum ether:EA (from 0% to 8%) providing methyl 3-iodo-2-methylbenzoate (1.7 g, 80.4% yield) as a colorless oil. MS (ESI) m/z 277.0 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 7.97 (dd, J = 1.2, 8.0 Hz, 1 H), 7.73 (dd, J = 0.8, 8.0 Hz, 1 H), 6.92 (t, J = 8.0 Hz, 1 H), 3.89 (s, 3 H), 2.66 (s, 3 H). |
75% | With thionyl chloride; at 0℃; for 3h;Reflux; | (W02006117669 (Al)): To a solution of 3-iodo-2-methylbenzoic acid (5.00 g, l9.08mmol) in MeOH (20 mL) was added dropwise a solution of SOCh (4.16 mL, 57.24 mmol) in MeOH (10 mL) at 0 C. The mixture was heated to reflux for 3 h. The mixture was concentrated and the residue obtained was purified using S1O2 chromatography eluting with EtOAc in hexanes (0-15% EtOAc, gradient elution) to provide the title compound 5 as a brown oil (4.00 g, 75%). 1H NMR (500 MHz, CDC13) d 8.00 (dd, J = 1.3, 7.9 Hz, 1H), 7.76 (dd, J = 1.3, 7.7 Hz, 1H), 6.95 (td, J = 0.7, 7.8 Hz, 1H), 3.93 (s, 3H), 2.69 (s, 3H). HPLC-MS (ESI+): m/z 276.9 [100%, (M+H)+], 761.3 [72%, (M+Na)+] |
sulfuric acid; for 40h;Heating / reflux; | Example 19{fl-Cyano-4-hydroxy-8-(4-methoxy-phenoxy)-isoquinoline-3-carbonyll-amino}-acetic acid a. 3-Iodo-2-methyl-benzoic acid methyl ester[0235] A mixture of 3-iodo-2-methyl-benzoic acid (90 mmol, 23.6 g), methanol (250 mL), and concentrated sulfuric acid (13 mL) was re fluxed with stirring for 40 h before it was concentrated in vacuo. The residue was dissolved in ethyl acetate and the mixture was neutralized by adding small portions of a saturated aqueous NaHCOs solution with stirring. The organic phase was dried over MgSO4 and concentrated in vacuo to give the title compound as a yellowish oil (24.3 g); 1H NMR (CDCl3, 200 MHz): delta = 7.96 (d, 1 H), 7.71 (d, 1 H), 6.91 (t, 1 H), 3.89 (s, 3 H), 2.66 (s, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48.4% | With palladium diacetate; sodium carbonate; In N,N-dimethyl acetamide; at 20 - 120℃; for 10h;Inert atmosphere; | [0470] To a solution of <strong>[52570-33-9]methyl <strong>[52570-33-9]3-iodo-2-methylbenzoate</strong></strong> (15 g, 54.35 mmol) in N,N-dimethylacetamide (200 mL) at rt was added K4[Fe(CN)6].3H2O (5.74 g, 13.59 mmol) and sodium carbonate (5.76 g, 54.35 mmol), followed by palladium acetate (1.5 g) added. The suspension was evacuated and replaced with nitrogen, then heated to 120C for 10 hrs. The reaction mixture was cooled to rt, filtered, and the filtrate was diluted with water (100 mL), and extracted with EA (200 mL) twice. The combined organic layers were washed with water, brine, dried over sodium sulfate, filtered and concentrated providing the crude product, which was purified by column chromatography on silica-gel elution with petroleum ether:EA (from 50/1 to 30/1) providing methyl 3-cyano-2-methylbenzoate (4.6 g, 48.4% yield) as a white solid. MS (ESI) m/z 175.9 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 8.08 (d, J = 7.6 Hz, 1 H), 7.76 (d, J = 8.0 Hz, 1 H), 7.36 (t, J = 7.6 Hz, 1 H), 3.93 (s, 3 H), 2.80 (s, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With palladium diacetate; potassium carbonate; triphenylphosphine; In N,N-dimethyl-formamide; at 100℃; for 12h;Inert atmosphere; | 0.2 mmol of potassium carbonate and 0.01 mmol of palladium acetate.0.02 mmol of triphenylphosphine, 0.2 mmol of methyl 2,3-dicarboxylate-7-oxanorbornadiene,2-fluoro-3-carboxylic acid methyl ester iodobenzene 0.1 mmol, hexamethyldisiloxane 0.15 mmol,1 mL of N,N-dimethylformamide was added to a 15 mL reaction tube.Nitrogen was repeatedly filled 3 times, placed in an oil bath at 100 C, and reacted for 12 h;After cooling to room temperature, the reaction solution was diluted with ethyl acetate and washed with water three times.The organic phase was dried over anhydrous Na2SO4, filtered and concentrated.Purified by column chromatography19.2mg of target product,The yield was 60%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With palladium diacetate; caesium carbonate; triphenylphosphine; In N,N-dimethyl-formamide; at 100℃; for 12h;Inert atmosphere; | 0.2 mmol of cesium carbonate, 0.01 mmol of palladium acetate, 0.02 mmol of triphenylphosphine,1,4-Dihydro-1,4-epoxy naphthalene 0.2 mmol, <strong>[52570-33-9]methyl <strong>[52570-33-9]3-iodo-2-methylbenzoate</strong></strong> 0.1 mmol,0.15 mmol of hexamethyldisilazide and 1 ml of N,N-dimethylformamide were added to a 15 ml reaction tube.Nitrogen was repeatedly filled 3 times, placed in an oil bath at 100 C, reacted for 12 h; cooled to room temperature,The reaction solution was diluted with ethyl acetate and washed with water three times.The organic phase is dried over anhydrous Na2SO4.Filtered, concentrated, and purified by column chromatography34.8 mg of the target product in a yield of 79%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With palladium diacetate; sodium carbonate; bis[2-(diphenylphosphino)phenyl] ether; In N,N-dimethyl-formamide; at 100℃; for 24h;Inert atmosphere; | 0.3 mmol of sodium carbonate, 0.1 mmol of diphenylacetylene, and 0.005 mmol of palladium acetate.Bis(2-diphenylphosphinophenyl)ether 0.005 mmol, hexamethyldisilane 0.15 mmol,0.15 mmol of <strong>[52570-33-9]methyl <strong>[52570-33-9]3-iodo-2-methylbenzoate</strong></strong> and 1 mL of N,N-dimethylformamide were added to a 15 mL reaction tube.Nitrogen was repeatedly filled 10 times, placed in an oil bath at 100 C, and reacted for 24 hours;Cooled to room temperature, the reaction was diluted with ethyl acetate, washed with water three times, the organic phase dried over anhydrous Na2SO4, filtered, and concentratedPurification by thin layer chromatography to give 24.6mg of the desired product, yield 52%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With palladium diacetate; potassium carbonate; triphenylphosphine; In N,N-dimethyl-formamide; at 100℃; for 16h;Inert atmosphere; | Add 0.2 mmol of potassium carbonate,0.01mmol of palladium acetate,Triphenylphosphine 0.02mmol,Methyl <strong>[52570-33-9]3-iodo-2-methylbenzoate</strong> 0.1 mmol,1-phenyl-1-pentyne 0.2 mmol and1 mL of N, N-dimethylformamide was added to a 15 mL reaction tube,Fill it repeatedly with nitrogen 10 times, stir at room temperature for 15min, and place in an oil bath at 100 C.Reaction for 16h; cooled to room temperature, the reaction solution was diluted with ethyl acetate, washed with water, the organic phase was dried over anhydrous Na2SO4, filtered, concentrated, and purified by thin layer chromatography to obtain 8.7mg of the target product,Colorless oil with a yield of 30%. |
Tags: 52570-33-9 synthesis path| 52570-33-9 SDS| 52570-33-9 COA| 52570-33-9 purity| 52570-33-9 application| 52570-33-9 NMR| 52570-33-9 COA| 52570-33-9 structure
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Code | Phrase |
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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 |
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