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CAS No. : | 43114-43-8 | MDL No. : | MFCD11052329 |
Formula : | C8H8O3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OVSMURBVBQUOSF-UHFFFAOYSA-N |
M.W : | 184.21 | Pubchem ID : | 13596602 |
Synonyms : |
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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 |
---|---|---|
With sodium tetrahydroborate; In ethanol; at 20℃; for 1h; | NaBH4 is added to a solution of 750 mg (4.08 mmol) 3-methanesulphonyl-benz- aldehyde in 20 ml ethanol (see P. L. ORNSTEIN, T. J. Bleisch, M. B. Arnold, R. A. Wright, B. G. Johnson, J. P. Tizzano, D. R. Helton, M. J. Kallman, D. D. SCHOEPP, M. Herin, J MED. Chem. 1998, 41 (3), 358-378 or B. Eistert, W. Schade, H. Selzer, Ber. 1964, 97 (5), 1470-81). The reaction mixture is stirred at room temperature for 1 h. The reaction mixture is poured into water and extracted three times with ethyl acetate. The combined organic layers are washed with water and brine, dried, filtered and concentrated in vacuo to afford the title compound, used in the next step without further purification. H-NMR (300 MHz, DMSO): 7.85 (broad s, 1H), 7.78 (d, 1H), 7.62 (d, 2H), 7.59 (t, 1H), 5.45 (t, 3H), 4.58 (d, 2H), 3.19 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With pyridinium chlorochromate; In dichloromethane; at 20℃; for 2h; | A solution of [3-(methylsulfonyl) phenyl] methanol (680 mg, 3.66 MMOL) IN anhydrous CH2CI2 (20 mL) was treated with PCC (1.03 g, 4.75 mmol) at room temperature for 2 hours. The solvent was removed and the residue was purified by flash column chromatography (20-60% EtOAc in hexanes) to give the product (500 mg, 74% YIELD). H NMR (300 MHz, CDC13) 5 : 3.13 (s, 3 H), 7.77-7. 82 (m, 1 H), 8.18-8. 24 (m, 2 H), 8.46-8. 48 (m, 1 H), 10.12 (s, 1 H). |
72% | With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; at 20℃; for 1h;Molecular sieve; | Solid tetrapropylammonium perruthenate ("TPAP", 0.05 mmol) was added in one portion to a stirred mixture of compound 8. 6 (1 mmoL), 4- methylmorpholine N-oxide ("NMO" ; 1.5 mmoL) and powdered 4A molecular sieve (equal weight to that of NMO) in 5 mL of DCM at room temperature under N2. The reaction mixture was stirred at room temperature. for 1 hour, and then filtered through a short pad of silica gel, eluting with mixture of DCM and AcOEt (1: 1). The filtrate was concentrated and the residue was purified with chromatography (Si02, AcOEt/hexane 2: 1) to afford compound 8.7 (yield 72%). 1H NMR (400 MHz, CDC13) 8 3.14 (s, 3 H), 7.81 (t, J=7. 58 Hz, 1 H), 8.21 (t, J=9. 05 Hz, 2 H), 8.46 (s, 1 H), 10.12 (s, 1 H) ppm. |
To a solution of oxalyl chloride (1.05 mL, 12 mmol) in DCM (15 mL) at -78C is added a solution of DMSO (1.9 mL, 26.6 mmol) in DCM (15 mL) over 5 minutes. The reaction mixture is stirred for 20 minutes, then a solution of <strong>[220798-39-0](3-methanesulfonyl-phenyl)-methanol</strong> (0.992 g, 5.33 mmol) in DCM (20 mL) is added over a 5 minute period. The reaction mixture is stirred for 15 minutes then Et3N (3.78 mL, 27.2 mmol) is added over a 5 minute period. The ice bath is removed and water (30 mL) is added at room temperature. The reaction mixture is stirred for 10 minutes, then the organic layer is isolated, dried over MgSO4 and EPO <DP n="34"/>filtered. The solvent is removed under reduced pressure to yield 3-methanesulfonyl- benzaldehyde as a pale orange solid; [M-H]" 183. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To an ice-cooled stirring suspension of NaH (60% dispersion in mineral oil; 0.23 g,6 mmol) in dry THF (25 ml_) under inert atmosphere is added dropwise diethyl (cyanomethyl)phosphonate (0.94 mL, 6 mmol). After 50 minutes at 00C, a solution of 3- methanesulfonyl-benzaldehyde (0.918 g, 5 mmol) in dry THF (5 mL) is added dropwise over a 10 minutes period at 00C. The reaction mixture is stirred at room temperature overnight. The solvent is removed under reduced pressure and the residue is partitioned between EtOAc and water. The aqueous phase is extracted with EtOAc and the organic phases are combined, washed with water, brine and dried over MgSO4 and the solvent is removed under reduced pressure to give 3-(3-methanesulfonylphenyl)-acrylonitrile as an orange sticky solid; [M-H]" 206. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 13; 7-{r?i?Vl-(EtavdroxymethylV3-methgammalbutyllamino}-5-({l-[3-(methylsulfonyl')phenyllethyl}thio>)ri,31thiazolor4,5-<i1pyrimidin-2C3H)-one; a) l-f3-(Methylsulfonyl)phenyl]ethanol; Methylmagnesium iodide (3M in THF3 13.2 mL, 4.4 mmol) was added dropwise via syringe at 0 0C to <strong>[43114-43-8]3-(methylsulfonyl)benzaldehyde</strong> (0.74 g, 4.0 mmol) in THF (15 mL). The resulting reaction mixture was stirred at 0 0C until no more conversion to product occurred (monitored by GC-MS). The reaction was quenched with saturated ammonium chloride, the aqueous phase was extracted with EtOAc and the organic phase was washed with saturated sodium bicarbonate, brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash column chromatography on silica (EtOAc: hexane 1 : 4) to give the title compound (260 mg) that was used in the next step without any further purification (approximate purity 50%).GC-MS (EI) (HP5MS, 0.25 mm x 30 m, 0.25 mum) m/z 200 M+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | The N, N, N', N',-tetramethylguanidine ("TMG" ; 1. 05 mmole) was added slowly to a solution of (d, l) -Cbz-a-phosphonoglycine trimethylester (1. 1 mmole) in 4 ml of DCM at room temperature. After 15 minutes, the mixture was cooled to- 30C and compound 8.7 (1 mmole) added dropwise. The mixture was kept at-30C for 20 minutes and slowly allowed to warm to 0C. The solution was diluted with AcOEt and washed consecutively with 1 N NaHS04 and brine. The solution was dried (Na2SO4), and solvent evaporated to provide crude product. Purification of thecrude product on chromatography (Si02, AcOEt/hexanes/DCM 3: 3: 1) to give product 8.8 (yield 72%). 1H NMR (400 MHz, CDC13) 6 2.97 (s, 3 H), 3.86 (s, 3 H), 5.08 (s, 2 H), 6.78 (s, 1 H), 7.34 (d, J=6. 36 Hz, 5 H), 7.50 (t, J=7. 83 Hz, 1 H), 7.72 (d, J=7. 34 Hz, 1 H), 7.85 (d, J=7. 34 Hz, 1 H), 8.04 (s, 1 H). Olefinic proton in the minor trans isomer at 7.19 ppm (s, 1H). ESI-MS (mlz) : (M+H+) 346. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With ytterbium(III) trifluoromethanesulfonate hydrate; In acetonitrile; at 90℃; for 12h;sealed reaction bottle; | A mixture of 4-aminobenzoic acid ethyl ester (3.3 g, 20 mmol), <strong>[43114-43-8]3-methanesulfonyl benzaldehyde</strong> (3.68 g, 20 mmol) and ytterbium(III) triflate hydrate (1.86 g, 3 mmol) in acetonitrile (150 mL) was cooled to 0 C. in a sealed reaction bottle. Then a cooled solution of isobutene (5.6 g, 100 mmol) was added into. The reaction mixture was heated to 90 C. and stirred for 12 h. The solvent was removed in vacuo and the residue was purified on flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (10% ethyl acetate/hexanes) to afford 2-(3-methanesulfonyl-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (3.3 g, 43%) as a white solid: MS (ESI) M+1=388.3. |
43% | ytterbium(III) trifluoromethanesulfonate hydrate; In acetonitrile; at 0 - 90℃; for 12h;Sealed tube; | Example 37 N- [2- (3-methanesulf onyl-phenyl) -4,4-dimethyl- 1 ,2,3,4- tetrahydro- quinoline-6- carbonyl] -methanesulfonamideA mixture of 4-aminobenzoic acid ethyl ester (3.3 g, 20 mmol), <strong>[43114-43-8]3-methanesulfonyl benzaldehyde</strong> (3.68 g, 20 mmol) and ytterbium(III) triflate hydrate (1.86g, 3 mmol) in acetonitrile (150 mL) was cooled to 0 C in a sealed reaction bottle. Then a cooled solution of isobutene (5.6 g, 100 mmol) was added into. The reaction mixture was heated to 90 C and stirred for 12 h. The solvent was removed in vacuo and the residue was purified on flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company)(10% ethyl acetate/hexanes) to afford 2-(3-methanesulfonyl- phenyl)-4,4-dimethyl-l,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (3.3 g, 43%) as a white solid: MS(ESI) M+l = 388.3.A mixture of 2-(3-methanesulfonyl-phenyl)-4,4-dimethyl-l,2,3,4-tetrahydro-quinoline-6- carboxylic acid ethyl ester (3.3 g, 8.53 mmol), sodium hydroxide (3.41 g, 85.3 mmol), water (10 mL) in acetonitrile (30 mL) was stirred at 60C for 12 h. The mixture was neutralized with a 3 mol/L aqueous hydrochloric acid solution and extracted with ethyl acetate (2 x 50 mL), washed with water, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-(3-methanesulfonyl-phenyl)-4,4-dimethyl-l,2,3,4- tetrahydro-quinoline-6-carboxylic acid (2.76 g, 90%) as a white solid which was used for next step without further purification: MS(ESI) M+l = 360.3.To a suspension of methanesulfonamide (480 mg, 5.0 mmol) in N,N-dimethylformamide (5 mL) was added sodium hydride (200 mg, 5.0 mmol). The resulting mixture was stirred at 25C for 1 h to afford Solution A37. A solution of 2-(3-methanesulfonyl-phenyl)-4,4- dimethyl- 1, 2,3, 4-tetrahydro-quinoline-6-carboxylic acid (359 mg, 1.0 mmol) and 1,1'- carbonyldiimidazole (320 mg, 2.0 mmol) in N,N-dimethylformamide (5 mL) was stirred at 70C for 1 h and cooled to room temperature to afford Solution B37. Solution B37 was added to Solution A37 and the resulting mixture was stirred at 25C for 1 h. To the reaction mixture was added water (0.5 mL). The mixture was filtered to remove the insoluble solid, and the filtrate was purified by Waters automated flash system (column: Xterra 30 mm x 100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded N-[2- (3-methanesulfonyl-phenyl)-4,4-dimethyl-l,2,3,4-tetrahydro-quinoline-6-carbonyl]- methanesulfonamide (100 mg, 23%) as a white solid: MS(ESI) M+l = 437.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 127: ffl-(1-(2-(3-(Methylsulfonyl)phenyl)-3H-imidazor4,5-blpyridin-5- yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone To a solution of ^-(^(S^-diaminopyridin^-y piperidin-S-y^pyrrolidin-l-y methanone dihydrochloride (125 mg, 0.3 mmol) in anhydrous /V,/V-dimethylformamide (2.5 mL) was added <strong>[43114-43-8]3-(methylsulfonyl)benzaldehyde</strong> (76 mg, 0.4 mmol). The solution was stirred at 80C for 1 h. Sulfur was added (25 mg, 0.8 mmol) followed by triethylamine (140 mu, 1.0 mmol). The mixture was stirred at 85C for 24 h followed by stirring at room temperature for another 24 h. The mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane and water. The aqueous layer was extracted with dichloromethane and the combined extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified via flash chromatography (20-100% ethyl acetate in heptanes gradient followed by 0-10% methanol in dichloromethane). The residue was repurified via flash chromatography (0-10% methanol in dichloromethane) to afford a yellow solid that was stirred in acetonitrile (3 ml.) at 40C for 2.5 h. The solid was filtered, washed with cold acetonitrile and dried under high vacuum at 40C to afford the title compound. 1H NMR (500 MHz, CD3OD) 5 1.60-1.74 (m, 1 H) 1.77-1 .89 (m, 2H) 1.89-2.1 1 (m, 4H) 2.81 (br s, 1 H) 2.97-3.09 (m, 2H) 3.17-3.26 (m, 3H) 3.41-3.52 (m, 2H) 3.52-3.63 (m, 1 H) 3.74 (br s, 1 H) 4.37 (br s, 1 H) 4.64 (d, 1 H) 6.91 (br s, 1 H) 7.74-7.89 (m, 2H) 8.05 (d, 1 H) 8.35 (br s, 1 H) 8.65 (br s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | To a stirred solution of <strong>[43114-43-8]3-(methylsulfonyl)benzaldehyde</strong> (114a) (1 g, 5.43 rnrnol) in tetrahydrofuran (10 mL) was added (3-(bis(trirnethylsilyl)amino )phenyl )magnesi urnchloride (49c) (6.51 rnL, 6.51 rnmol) at 0C. The reaction was stirred for 14 hat same temperature and quenched by adding 2 N HCI (13.57 mL, 13.57 mmol), stirred for 6 h. The reaction mixture was treated with 2 N NaOH (1 5 mL) and extracted with ethyl acetate (2 x 50 mL). The organic layers were combined washed with sat. NH4CI (50 mL), dried over anhydrous MgSO4, filtered, evaporated to dryness. The crude residue was purified by flashcolumn chromatography (silica gel 40 g, eluting with ethyl acetate in hexane from 0-100%)to furnish (3-aminophenyl)(3-(methylsulfonyl)phenyl)methanol (I 14b) (1.004 g, 67%) as a white gum; ?H NMR (300 MHz, DMSO-d6) 6 7.93 (t, .1 1.7 Hz, I H), 7.77 (dt. .1 7.6, 1.5 Hz, IH), 7.66 (dt,J= 7.7, 1.5 Hz, IH), 7.57 (t,.J= 7.7 Hz, 1H), 6.94 (t,.J?? 7.7 Hz, 1H), 6.580,J= 1.9Hz, IH),6.53 (dtJ=7.5, 1.3 Hz, .IH),6.40(ddd,J=8.0,2.3, 1.1 Hz, IH),5.99 (d, .1= 3.8 Hz, I H), 5.63 (d, .1 = 3.8 Hz, 1 H), 5.05 (s, 2H), 3.20 (s, 3H); MS (ES+):278.1 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In ethanol; at 40℃; | General procedure: Benzohydrazide (1.0 equiv) and various benzaldehydes (a-m, 1.5 equiv) were dissolved in anhydrous ethanol (5 mL) and stirred at 40 C for overnight. The solvent was removed under vacuum. The product was obtained as yellow solid, which was filtered and washed with ethyl ether. Remained benzaldehyde was washed out by ethyl ether. (Yield; 80-85%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A solution of tert-Butyl 6-benzyloxy-7-methoxy-1-[(1-phenyltetrazol-5-yl)sulfonylmethyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate (100 mg, 0.169 mmol) and <strong>[43114-43-8]3-methylsulfonylbenzaldehyde</strong> (155 mg, 0.84 mmol) in THF (10 mL) was cooled to -35 C. with stirring under argon. To this mixture was added a solution of lithium bis(trimethylsilyl)amide (0.68 mL, 0.68 mmol, 1M in THF) and the reaction mixture was stirred for 1 hour at -35 C. The reaction was allowed to warm up to room temperature and the organic solvent was evaporated to give a residue. The residue was dissolved (or suspended) in 4M HCl dioxane (5 mL) and stirred at room temperature until the reaction was completed. The organic layer was evaporated to leave a residue, which was purified by flash or reverse phase preparatory chromatography. LC-MS; M+1=450. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | 1. To a solution of 2-chlorothiazole (0.72 g, 6.00 mmol) in dry THF (50 mL) at -78 "C under N2 was added n-BuLi (2.4M, 2 5 mL, 6 mmol) dropwise. After 0 5 h a solution of 1 (1.00 g, 5.43 mmol) in dry THF (5 mL) was added dropwise. The reaction was slowly warmed to RT. The reaction was quenched with saturated NH4C1 and extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SC>4, filtered and the filtrate concentrated to give a crude product which was purified by silica gel chromatography to afford 2 (0.60 g, 36% yield) as a yellow oil. MS (ESI): mass calcd. for C11H10CINO3S2 303.78, m/z found 304.1 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium tert-butylate; In tetrahydrofuran; tert-butyl alcohol; at 20℃; for 2h; | Aryl aldehyde (20 mmol, 1.0 eq) and nitromethane (32 mmol, 1.6 eq) were dissolved in tBuOH/THF (l5mL/15mL) at rt. Then tBuOK (2 mmol, 0.1 eq) was added and the resulting mixture was stirred for 2 h. Next, it was poured into water and extracted 3x with ethyl acetate. The combined organic phase was then dried over anhydrous NaiSCU and concentrated to afford crude b-hydroxyl nitroalkane, which was directly dissolved in DCM. DMAP (1 mmol, 0.05 eq) was then added, and the mixture was stirred and cooled in ice- water bath. AC20 (22 mmol, 1.1 eq) was added dropwise before ice-water bath was removed. The mixture was stirred for additional 2 h and LC-MS indicated formation of desired nitroalkene. The mixture was poured into saturated NaHCCb and extracted 3x with DCM. The combined organic phase was dried over anhydrous Na2S04 and concentrated to afford crude product and purified via silica gel flash chromatography. |
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