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CAS No. : | 886762-70-5 | MDL No. : | MFCD07368788 |
Formula : | C6H3BrFNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VFPAOFBPEYCAAZ-UHFFFAOYSA-N |
M.W : | 220.00 | Pubchem ID : | 2783152 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 42.92 |
TPSA : | 45.82 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.84 cm/s |
Log Po/w (iLOGP) : | 1.44 |
Log Po/w (XLOGP3) : | 2.54 |
Log Po/w (WLOGP) : | 2.92 |
Log Po/w (MLOGP) : | 2.87 |
Log Po/w (SILICOS-IT) : | 0.81 |
Consensus Log Po/w : | 2.12 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.14 |
Solubility : | 0.159 mg/ml ; 0.000721 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.15 |
Solubility : | 0.156 mg/ml ; 0.000709 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.92 |
Solubility : | 0.266 mg/ml ; 0.00121 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.85 |
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 |
---|---|---|
80% | In tetrahydrofuran; at 20℃; | Example A23 a) Preparation of intermediate 53Benzylamine (17 g, 159 mmol) was added to a sol. of l-bromo-3-fluoro-2-nitro- benzene (10 g, 45.5 mmol) in THF (100 ml). The r.m. was stirred at r.t. overnight. The formed precipitate was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was dissolved in DCM and the resulting sol. was washed subsequently with an aq. AcOH sol, a saturated aq. NaHCO3 sol, and water. The - -organic layer was dried (MgSO4), filtered and concentrated in vacuo. The crude residue was dissolved in AcOH (10OmL) and iron powder (7.62 g, 136 mmol) was added. The resulting suspension was stirred and heated at 60 0C for 1 h. The r.m. was concentrated in vacuo and the residue was partitioned between DCM and a saturated aq. NaHCO3 sol. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Yield: 6.5 g of intermediate 53 (80 % purity according to LC-MS analysis), which was used as such in the next reaction step. |
With potassium carbonate; at 20℃; for 18h; | Potassium carbonate (2.58 g, 18.73 mmol) was added to a solution of of <strong>[886762-70-5]1-bromo-3-fluoro-2-nitro-benzene</strong> (2.06 g, 9.36 mmol) and benzylamine (1.13 mL, 9.364 mmol) and the resulting suspension was stirred at room temperature for 18 hours. The reaction mixture was poured onto 500 mL of ice water and extracted four times with 100 mL ethyl acetate. The combined organic fractions were dried over sodium sulfate, and concentrated in vacuo to give an oil that was purified by recrystallization from 75 mL refluxing ethanol with 3 mL water. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; acetic acid; at 55℃; for 4h; | To a suspension of sodium perborate tetrahydrate (135.374 g., 886.4 mmol) in 500 mL acetic acid at 55 C. was added dropwise a solution of <strong>[65896-11-9]2-bromo-6-fluoro-phenylamine</strong> (33.685 g., 177.271 mmol) in 70 mL acetic acid over 1 hour. The reaction mixture was stirred at 55 C. for an additional 3 hours, then cooled to 0 C. in an ice bath. Insoluble materials were removed by filtration through a plug of celite, which was rinsed with 100 mL acetic acid. The combined acetic acid fractions were added to 3 L ice water with stirring to give a waxy solid which was removed by filtration. The crude solid was dissolved in 250 mL ethyl acetate, washed three times with 200 mL of 10% aqueous hydrogen chloride, 200 mL saturated sodium bicarbonate and 100 mL brine. The solution was concentrated in vacuo to give 11.51 g of 1-bromo-3-fluoro-2-nitro-benzene as a red oil, 1H NMR (CDCl3, 300 MHz) delta: 7.26 (m, 1H), 7.38 (m, 1H), 7.49 (m, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl acetamide; at 80℃;Sealed tube; | 1-Bromo-3-fluoro-2-nitrobenzene (10.25 g, 46.6 mmol), ethyl glycinate hydrochloride (7.15 g, 51.3mmol), DIPEA (24.45 mL, 140 mmol) in DMA (116 mL) were sealed within a vessel and heated to 80 Cfor 8 h. The reaction mixture was diluted with DCM (400 mL) and washed with water (4 x 200 mL). Theorganic layers were combined, passed through a hydrophobic frit and the solvent was removed invacuo. The residue was dissolved in DCM (10 mL) and split into two equal portions. Each portion waspurified by normal phase chromatography (0 - 70 % EtOAc in cyclohexane, 120 g SiO2) and combinedto afford ethyl (3-bromo-2-nitrophenyl)glycinate (10.90 g, 36.0 mmol, 77 % yield) as an orange solid.M.pt.: 83 - 85 C; numax (neat): 3409, 2993, 1728, 1522, 1501 cm1; 1H NMR (400 MHz, DMSO-d6) delta =7.24 (1H, t, J = 8.1 Hz), 7.00 (1H, d, J = 7.8 Hz), 6.78 (1H, d, J = 8.3 Hz), 6.52 (1H, t, J = 6.1 Hz), 4.12 (2H,q, J = 7.0 Hz), 4.03 (2H, d, J = 5.9 Hz), 1.19 (3H, t, J = 7.1 Hz); 13C NMR (101 MHz, DMSO-d6) delta = 170.5, 142.2, 137.9, 133.1, 120.8, 114.1, 113.6, 61.1, 44.7, 14.5; LCMS (Method A): tR = 1.19 min, [M+H]+ 303& 305 (99 % purity); HRMS: (C10H11BrN2O4) [M+H]+ requires 302.9980, found [M+H]+ 302.9976. |
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl acetamide; at 20 - 80℃; for 16h; | 9.90 g (69.6 mmol) ethylglycinate hydrochloride are suspended under argon in 100 ml. of dry DMA. 24.3 ml_ (139 mmol) diisopropylethylamine and 10.21 g (46.4 mmol) of 2-bromo-6- fluoronitrobenzene are then added at RT. The orange solution is then heated to 800C for 16h. After cooling, the reaction mixture is poured onto iced-cold water and the suspension is collected by filtration to afford, after drying in HV at 5O0C, the title compound as a dark orange solid, which is used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; | 1.1 g of phenylboronic acid (9.0 mmol), 167 mg of 1,1'-bis(diphenylphosphino)ferrocenepalladium chloride (C35H30Cl4FeP2Pd, MW 816.65, 0.025 mmol) and 10.7 g of caesium carbonate (32.7 mmol) are introduced into a 250 mL round-bottomed flask, with stirring under an argon atmosphere, containing 54 mL of water, 18 mL of dioxane and 1.8 g of 39 (8.18 mmol). The medium is heated at 100 C., with stirring, for 1 h. The dioxane is concentrated, and extracted twice with 50 ml of AcOEt. The combined organic phases are dried over MgSO4, filtered and evaporated to dryness. 1.34 g of expected product 40 (yellow oil) are obtained.1H NMR (300 MHz, DMSO-d6), delta(ppm): 7.40 (m, 2H); from 7.42 to 7.56 (m, 4H); 7.66 (dt, J=2.0 and 9.0 Hz, 1H); 7.78 (dt, J=6.0 and 9.0 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In ethanol; | An 8 M methylamine sol. in ethanol (100 ml, 0.8 mol) was added to l-bromo-3-fluoro- 2-nitro-benzene (19.8 g, 90 mmol). The mixture was cooled on a water bath and was stirred overnight at r.t. Then, the solvent was evaporated and the residue was partitioned between water and DCM. The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. Yield: 20 g of intermediate 17 (96 %), which was used as such in the next step. |
96% | In ethanol; at 20℃; | Example A4 a) Preparation of intermediate 10A 8 M methylamine sol. in EtOH (100 ml, 0.8 mol) was added to l-bromo-3-fluoro-2- nitro-benzene (19.8 g, 90 mmol), cooled on a water bath. The r.m. was stirred at r.t. overnight. Then, the solvent was evaporated and the residue was partitioned between water and DCM. The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. Yield: 20 g of intermediate 10 (96 %), which was used as such in the next reaction step. |
In tetrahydrofuran; at 80℃; for 2h; | A solution of i-bromo-3-fluoro-2-nitrobenzene(iO g, 45.6 mmol) in NH2CH3 inTHF (2 M, 100 ml) was stirred at 80C for 2 hr. The reaction mixture was concentrated undervacuumto give 3-bromo-N-methyl-2-nitrobenzenamine. LCMS (ESI) calc?d forC7H7BrN2O2[M+ i]: 231, found [M+i]: 231, ?H NMR (CDC13, 400 MHZ): 7.21-7.16 (m, iH), 6.97 (d, J 7.6Hz, iH), 6.76 (d, J= 7.6 Hz, iH), 2.94 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.34% | In ethanol; at 50℃; for 48h; | The solution of <strong>[886762-70-5]1-bromo-3-fluoro-2-nitrobenzene</strong> (4.5 g, 20.45 mmol) andisopropyl amine (1.21 g, 20.45 mmol) in EtOH (20 mL) was stirred at 50C for 48h. Thesolvent was removed in vacuo. The residue was purified by column (PE: EA '" 10:1) to givecompound 103A (5 g, yield: 94.34%) as brown oil. |
94.34% | In ethanol; at 50℃; for 48h; | The solution of l-bromo-3-fluoro-2-nitrobenzene (4.5 g, 20.45 mmol) and isopropyl amine (1.21 g, 20.45 mmol) in EtOH (20 mL) was stirred at 50C for 48h. The solvent was removed in vacuo. The residue was purified by column (PE: EA = 10:1) to give compound 103A (5 g, yield: 94.34%) as brown oil. |
88% | In ethanol; at 20℃; | Isopropylamine (12.9 g, 218 mmol) was added to a sol. of l-bromo-3-fluoro-2-nitro- benzene (8.0 g, 36 mmol) in EtOH (40 mL). The r.m. was stirred at r.t. overnight. Then, the solvent was evaporated and the residue was partitioned between water and DCM. The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. Yield: 8.3 g of intermediate 32 (88 %), which was used as such in the next step |
88% | In ethanol; at 20℃; | Example A8 a) Preparation of intermediate 18Isopropylamine (12.9 g, 218 mmol) was added to a sol. of l-bromo-3-fluoro-2-nitro- benzene (8.0 g, 36 mmol) in EtOH (40 ml). The r.m. was stirred at r.t. overnight. Then, the solvent was evaporated and the residue was partitioned between water and DCM. The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. Yield: 8.3 g of intermediate 18 (88 %), which was used as such in the next reaction step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | General procedure: A 1 M stock of the zincate was prepared as follows: To a suspension of zinc powder (196 mg, 2.0 equiv, based on the iodoserine, dried under vacuum using a heat gun) was added DMF (0.7 mL) and catalytic iodine (50 mg, 0.19 mmol). The reaction mixture turned from colorless to red to colorless again in ?2 min. After the return to colorless a DMF solution (1.9 mL) of the iodoserine was added followed by additional iodine (50 mg). The reaction turned from pale yellow to red, and back to colorless with an associated exotherm. The solution was stirred until the exotherm subsided, was cooled to room temp (?25 min) and was stirred until the iodoserine disappeared as monitored by TLC. The zincate solution was syringed away from the excess zinc and was added to a separate flask containing Pd(OAc)2 (4 mg, 0.018 mmol), X-Phos (15 mg, 0.032 mmol), and the aryl bromide (1.88 mmol) in DMF (0.5 mL). The resulting mixture was stirred at room temperature overnight. Upon completion as indicated by TLC, the reaction was quenched with satd NH4Cl (10 mL), poured into H2O (50 mL) and extracted with EtOAc (2 × 50 mL). The organic layers were washed with H2O (2 × 100 mL), brine (1 × 100 mL), dried over MgSO4, filtered, and concentrated to a crude oil. The desired material was isolated via flash chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 70℃;Inert atmosphere; | Example 294-Bromo-l-[(3S)-l-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2-(4'-fluoro-4- biphenylyl)-lH-benzimidazole(a) 1,1-Dimethylethyl (3S)-3-[(3-bromo-2-nitrophenyl)amino]methyl}-l- pyrrolidinecarboxylateTo a solution of 1 , 1 -dimethylethyl (35)-3 -(aminomethyl)- 1 -pyrrolidinecarboxylate (1.15 g) in 50 mL dry DMSO was added DIEA (5.35 g) and l-bromo-3-fluoro-2-ntirobenzene (5 g). The flask was purged with nitrogen and heated at 70 C overnight. The reaction mixture was allowed to cool and was then diluted with diethyl ether, washed with brine and dried over sodium sulfate. The solvent was removed by evaporation and the crude product purified by silica gel column chromatography using petroleum ether/EtOAC to afford 6.5 g of the titled product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; In ethanol; water; for 5h;Reflux; | INTERMEDIATE (8-Bromo-3-methyl-quinoxalin-2-yl)-hydrazine (lid). A mixture of l-bromo-3- fluoro-2-nitro-benzene (99 g), racemic alanine (120 g) and CS2CO3 (440 g) in ethanol (1.2 L) and water (400 niL) was refluxed for 5h. After cooling to ambient temperature, the mixture was diluted with water (600 mL) and acidified to pH 3. The precipitate solid was collected and dried to afford racemic 2-(3-bromo-2-nitro-phenylamino)-propionic acid (110 g) as a yellow solid. lOg of this material in acetic acid (35 mL) and treated with iron powder (5.8 g) at 90 C for 2h, cooled and filtered then most of the acetic acid was removed in vacuo. The remaining slurry was extracted with DCM, dried over Na2S04, filtered, and concentrated in vacuo to afford 8-bromo-3- methyl-3,4-dihydro-lH-quinoxalin-2-one (6.4 g) as a yellow solid. A larger portion of this material prepared in a similar manner (29.2 g) was dissolved in 5% aq NaOH and treated with 30% aq hydrogen peroxide (140 mL) and water (180 mL). The mixture was stirred at 60 C for 6h before it was cooled. The precipitate solid was filtered off, washed with water, and dried to afford 8-bromo-3 -methyl- lH-quinoxalin-2-one (28.0 g). 21 g of this material was stirred in PI1POCI2 (80 mL) at 150 C for 4h. After cooling, water was added to quench excess PI1POCI2 and pH was subsequently adjusted to 7 with aq ammonia. The precipitated solid was filtered off, washed with water, and dried to afford 5-bromo-3-chloro-2-methyl-quinoxaline (17.7 g) as a yellow solid. This material was dissolved in ethanol (250 mL) was treated with hydrazine hydrate (160 mL) at reflux for 3h. Most of the volatiles were removed in vacuo. The precipitated solid was filtered off, washed with water, and dried to afford lid (14.8 g) as a yellow solid sufficiently pure for the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water; at 80℃;Inert atmosphere; | To a mixture of <strong>[886762-70-5]1-bromo-3-fluoro-2-nitrobenzene</strong> (0.953 g, 4.33 mmol) in a 100 mL round-bottomed flask equipped with a magnetic stir bar and nitrogen inlet were added dioxane (17.3 mL), sodium carbonate (0.551 g, 5.20 mmol), water (4.33 mL), and 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (0.977 mL, 5.20 mmol). To this mixture was added bis(triphenyl-phosphine)palladium(II)chloride (0.243 g, 0.347 mmol). The flask was evacuated and purged with nitrogen (3×) and then heated to 80 C. and stirred overnight. The reaction was cooled to room temperature, filtered through Celite, and the pad was washed with ethyl acetate. The phases were separated and the organic phase was concentrated. Purification by flash column chromatography provided the title compound (0.590 g, 3.26 mmol, 75% yield) as a light yellow oil: 1H NMR (400 MHz, CDCl3) delta 7.48-7.36 (m, 1H), 7.21-7.06 (m, 2H), 5.23 (p, J=1.5 Hz, 1H), 5.05 (q, J=1.1 Hz, 1H), 2.09 (s, 3H); 13C NMR (101 MHz, CDCl3) delta 153.56 (d, JCF=257.5 Hz), 139.62, 139.60, 138.83, 131.48 (d, TCF=8.6 Hz), 124.47 (d, JCF=3.6 Hz), 117.60, 115.51 (d, JCF=19.1 Hz), 23.18. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl acetamide; at 20℃; for 0.25h; | DIPEA (45.1 mL, 259 mmol) was added to a stirred solution of L-alanine ethyl ester hydrochloride (Aldrich; 34.1 g, 222 mmol) and l-bromo-3-fluoro-2-nitrobenzene (126a; Ark Pharm, Inc., Libertyville, IL; 16.29 g, 74.0 mmol) in AyV-dimethylacetamide (15 mL) and the resulting yellow solution was stirred at RT for 15 min. A water-cooled reflux condenser was attached to the flask, and the resulting mixture was heated at 80 C for 18 h. The reaction was cooled to RT, diluted with saturated aq. NH4C1 (100 mL), and extracted with EtOAc (4 chi 75 mL). The combined organic extracts were dried over Na2S04, filtered, and concentrated in vacuo to provide (5)-ethyl 2-((3-bromo-2- nitrophenyl)amino)propanoate (126b; 24.1 g) as a brown residue (contains 10% starting material by LCMS and H NMR), which was used directly in the subsequent step: H NMR (400 MHz, CDCl3) delta ppm 7.13 (1 H, t, J=8.2 Hz), 7.00 (1 H, d, J=8.0 Hz), 6.64 (1 H, d, J=8.4 Hz), 5.89 (1 H, d, J=6.8 Hz), 4.22 (2 H, m, .7=7.0, 7.0, 7.0 Hz), 4.14 (1 H, quin, J=7.1 Hz), 1.51 (3 H, d, J=7.0 Hz), 1.27 (3 H, t, .7=7.1 Hz), m/z (ESI, +ve) 317.0 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tris-(dibenzylideneacetone)dipalladium(0); monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; In tetrahydrofuran; diethyl ether; at 20℃; for 0.75h;Inert atmosphere; | To a solution of <strong>[886762-70-5]1-bromo-3-fluoro-2-nitrobenzene</strong> (CAS 886762-70-5) (110 mg, 0.500 mmol) in THF (2.00 ml) under nitrogen was added Pd(dba)2 (CAS 32005-36-0) (14.4 mg, 0.025 mmol) and Q-Phos (CAS 312959-24-3) (17.8 mg, 0.025 mmol), then lastly (2-(tert- butoxy)-2-oxoethyl)zinc(ll) chloride (CAS 321745-86-2) (0.5M in Ether, 1.10 ml, 0.550 mmol) and the reaction stirred at rt. After 45 minutes the reaction was purified directly by flash chromatography (0-40% EtOAc: Heptanes) to provide the title compound. MS (ESI-) m/z 254.2 (M-H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In ethanol; at 20℃; for 15h; | To a solution of <strong>[886762-70-5]1-bromo-3-fluoro-2-nitrobenzene</strong> (40a; 500 mg, 2.27 mmol) in EtOH (2.5 mL) was added ethanamine(753 mg, 11.4 mmol), and the mixture was stirred at room temperature for 15 h. The mixture was concentrated in vacuo, and the residue was partitioned between EtOAc and water. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo to give 41a (534 mg, 96%) as a red oil. 1HNMR (CDCl3) d 1.30 (t, 3H, J = 7.2 Hz), 3.19-3.27 (m, 2H), 5.61 (brs, 1H), 6.73 (d, 1H, J = 8.6 Hz), 6.93 (dd, 1H, J = 7.8, 1.0 Hz), 7.13(dd, 1H, J = 8.6, 7.8 Hz); MS (ESI) m/z 245, 247 [M+H]+. |
In tetrahydrofuran; at 20 - 80℃; for 2h;Sealed tube; | To the solution of ethanamine in THF(2M) was added 1-bromo-3-fluoro-2- nitrobenzene (10 g, 54 mmol) at ambienttemperature. The resulting solution was stirred in sealed tube at 80C for 2 hr and then concentrated under vacuum to give the title compound as a solid:LCMS (ESI) calc?d for C8H9BrN2O2 [M + H]: 244, found 244;?H NMR (400 MHz, CDC13) oe 7.26 (t, J= 8.0 Hz,1H), 689 (d, J= 8.0 Hz, 1H), 6.71 (d, J= 8.2 Hz, 1H), 3.39 (q, J= 3.9 Hz, 2H), 1.45 (t,J= 3.9 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 110℃; for 8h; | Commercially available <strong>[886762-70-5]2-bromo-6-fluoro-nitrobenzene</strong> (1.5 g, 6.82 mmol) was combined with palladium(ll) acetate (0.16 g, 0.8 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.62 g, 0.8 mmol) and cesium carbonate (4.44 g, 13.64 mmol). To the mixture was then added degassed 1 ,4-dioxane (15 mL) and morpholine (0.84 g, 9.6 mmol). The reaction mixture was heated at ~1 10C in a sand-bath for 8 h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (150 mL), water, (20 mL) and brine (20 mL). The organic phase was separated, dried over Na2S04, filtered and the solvents were removed under reduced pressure. The residue was purified on HP-Sil SNAP cartridges using a Biotage Isolera One purification system employing an EtOAc/n-heptane gradient (5/95 -> 40/60) to afford the title compound as a yellow oil (0.65 g, 42 %). 1H-NMR (400 MHz, CDCI3): delta = 3.02-3.06 (m, 4H), 3.77-3.81 (m, 4H), 6.91 -6.97 (m, 2H), 7.36-7.44 (m, 1 H) |
42% | With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 110℃; for 8h; | (0699) Step A (0700) Commercially available <strong>[886762-70-5]2-bromo-6-fluoro-nitrobenzene</strong> (1.5 g, 6.82 mmol) was combined with palladium(II) acetate (0.16 g, 0.8 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.62 g, 0.8 mmol) and cesium carbonate (4.44 g, 13.64 mmol). To the mixture was then added degassed 1,4-dioxane (15 mL) and morpholine (0.84 g, 9.6 mmol). The reaction mixture was heated at 110 C. in a sand-bath for 8 h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (150 mL), water, (20 mL) and brine (20 mL). The organic phase was separated, dried over Na2SO4, filtered and the solvents were removed under reduced pressure. The residue was purified on HP-Sil SNAP cartridges using a Biotage Isolera One purification system employing an EtOAc/n-heptane gradient (5/95->40/60) to afford the title compound as a yellow oil (0.65 g, 42%). (0701) 1H-NMR (400 MHz, CDCl3): delta=3.02-3.06 (m, 4H), 3.77-3.81 (m, 4H), 6.91-6.97 (m, 2H), 7.36-7.44 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A mixture of <strong>[3685-23-2](cis)-4-aminocyclohexanecarboxylic acid</strong> (1.5 equiv.), N,N- diisopropylethylamine (3.2 equiv.), and 1-bromo-3-fluoro-2-nitro-benzene (1.0 equiv.) was stirred in MeOH at 120 C for 6 days. The mixture was poured into HCI (2 M) and extracted with DCMx3. The combined organics were dried and concentrated. The crude material was then suspended in MeOH, after which H2S04 (cone., 2.2 equiv.) was added carefully. The mixture was stirred at reflux for 20 h and was then poured into NaHC03 and extracted with DCM*3. The combined organics were dried, concentrated, and purified by silica gel chromatography which afforded methyl (cis)-4-(3-bromo-2-nitro- anilino)cyclohexanecarboxylate. LCMS [M+H]+ 357. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; | Step A: To a stirred solution of <strong>[72235-56-4]3-chloro-4-fluorobenzylamine</strong> (250 muL, 2.00 mmol, 1.2 eq) in DMF (6 mL) was added potassium carbonate (460 mg, 3.32 mmol, 2 eq) at room temperature. After 5 min, solid 1-bromo-3-fluoro-2-nitrobenzene (365 mg, 1.66 mmol, 1 eq) was added at room temperature. The reaction was stirred at room temperature overnight (12 hrs) and monitored by LCMS. Upon conversion to the aniline product, the reaction was quenched with 10% aqueous HCl and diluted with water, and then extracted with ethyl acetate (×2). The organic phase was washed with water and a brine solution, dried over magnesium sulfate, and concentrated to a dark solid. This crude 3-bromo-N-(3-chloro-4-fluorobenzyl)-2-nitroaniline was used without further purification on the subsequent step. |
Tags: 886762-70-5 synthesis path| 886762-70-5 SDS| 886762-70-5 COA| 886762-70-5 purity| 886762-70-5 application| 886762-70-5 NMR| 886762-70-5 COA| 886762-70-5 structure
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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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