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[ CAS No. 57598-34-2 ]

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2D
Chemical Structure| 57598-34-2
Chemical Structure| 57598-34-2
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Product Details of [ 57598-34-2 ]

CAS No. :57598-34-2MDL No. :MFCD14635681
Formula : C12H16BrNO2 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :286.17Pubchem ID :-
Synonyms :

Computed Properties of [ 57598-34-2 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 57598-34-2 ]

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Application In Synthesis of [ 57598-34-2 ]

  • Downstream synthetic route of [ 57598-34-2 ]

[ 57598-34-2 ] Synthesis Path-Downstream   1~7

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  • [ 57598-32-0 ]
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  • [ 57598-32-0 ]
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  • [ 57598-32-0 ]
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  • [ 57598-48-8 ]
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  • [ 25216-74-4 ]
  • [ 74-88-4 ]
  • [ 57598-34-2 ]
YieldReaction ConditionsOperation in experiment
100% 7.6 g (190 mmol) of 60% sodium hydride are added portionwise to a solution of 47 g (173 mmol) of tert-butyl (3-bromophenyl) methylcarbamate in 500 ml of dimethylformamide. After the evolution of gas has ceased, 54 ml (865 mmol) of methyl iodide are added and the reaction medium is stirred at room temperature for 5 hours. After addition of water, the medium is extracted with ethyl acetate. The ethyl acetate phase is washed thoroughly with water, dried over magnesium sulfate, filtered and evaporated. 49 g (100%) of tert- butyl (3-bromophenyl) methylcarbamate are obtained.
100% [0342] Sodium hydride (806 mg, 20.2 mmol) was added to a solution of tert-butyl N-(3- bromophenyl)carbamate (3.7 g, 13.5 mmol) in DMF (80 mL) at 0 C. After stirring for 0.5 h under N2, iodomethane (2.10 g, 14.8 mmol) was added and the resulting reaction was stirred at room temperature overnight under N2. The mixture was poured into water (100 mL) and extracted with EtOAc (50 mL x 2). The combined organic phases were washed with water (100 mL x 3), brine (100 mL), dried over Na2S04 and concentrated to afford the desired product (3.86 g, 100%) as a yellow oil. [0343] LC-MS (Agilent): 4.18 min; m/z calculated for Ci2Hi6BrN02 [M-56+H] +230.0, found 230.0 [0344] 1H NMR (400 MHz, CDCI3) d (ppm): 7.42 (s, 1H), 7.30-7.27 (m, 1H), 7.18 (d, J = 4.8 Hz, 2H), 3.24 (s, 3H), 1.46 (s, 9H).
95% To a solution of 114 g (447 mmol) of <strong>[25216-74-4]tert-butyl (3-bromophenyl)carbamate</strong> in 800 ml of DMF are added portionwise 19 g (475 mmol) of sodium hydride (60% in oil) and the reaction medium is stirred until the evolution of gas has ceased. 29.3 ml (470 mmol) of methyl iodide are added dropwise and stirring is continued for 18 hours. The reaction medium is poured into ice-cold water and extracted with ethyl acetate. The organic phase is separated out after settling of the phases, dried over magnesium sulfate and evaporated. 115 g of tert-butyl (3-bromophenyl)-N-methylcarbamate are obtained in a yield of 95%
95% Jb. tert-Butyl (3-bromophenyl) -N-methylcarbamate; To a solution of 114 g (447 mmol) of tert- butyl (3-bromophenyl) carbamate in 800 ml of DMF are added portionwise 19 g (475 mmol) of sodium hydride (60% in oil) and the reaction medium is stirred until the evolution of gas has ceased. 29.3 ml (470 mmol) of methyl iodide are added dropwise and stirring is continued for 18 hours. The reaction medium is poured into ice-water and extracted with ethyl acetate. The organic phase is separated out by settling of the phases, dried over magnesium sulfate and evaporated. 115 g of tert-butyl (3-bromophenyl) -N-methylcarbamate are obtained in a yield of 95% .
95% With sodium hydride; In DMF (N,N-dimethyl-formamide); for 18h; 19 g (475 mmol) of sodium hydride (60% in oil) are added.in small amounts to a solution of 114 g (447 mmol) of tert-butyl (3-bromobenzyl) carbamate in 800 ml of dimethylformamide and the reaction medium is stirred until evolution of gas has ceased. 29.3 ml (470 mmol) of methyl iodide are added dropwise and stirring is maintained for 18 hours. The reaction medium is poured into ice-cold water and extracted with ethyl acetate. The organic phase is separated by settling, dried over magnesium sulphate and evaporated. 115 g of tert-butyl (3-bromobenzyl)-N-methylcarbamate are obtained. Yield = 95%.
92 - 95% b-tert-Butyl (3-bromophenyl)-N-methylcarbamateTo a solution of 129 g (475 mmol) of <strong>[25216-74-4]tert-butyl (3-bromophenyl)carbamate</strong> in 800 mL of dimethylformamide are added portionwise 19 g (475 mmol) of sodium hydride (60% in oil) and the reaction medium is stirred until the evolution of gas has ceased. 29 mL (470 mmol) of methyl iodide are added dropwise and stirring is continued for 18 hours. The reaction medium is poured into ice-cold water and extracted with ethyl acetate. The organic phase is separated out after settling of the phases, dried over magnesium sulfate, filtered and evaporated. 115 g (95%) of tert-butyl (3-bromophenyl)-N-methylcarbamate are obtained.; e-tert-Butyl 3-bromophenyl-N-methylcarbamateTo a solution of 128 g (470 mmol) of <strong>[25216-74-4]tert-butyl 3-bromophenylcarbamate</strong> in 800 mL of dimethylformamide, 19 g (475 mmol) of sodium hydride (60% in oil) are added portionwise and the reaction medium is stirred until the evolution of gas has ceased. 29.3 mL (470 mmol) of methyl iodide are added dropwise and stirring is continued for 18 hours. The reaction medium is poured into ice-cold water and extracted with ethyl acetate. The organic phase is separated out after settling of the phases, dried over magnesium sulfate and evaporated. 152.5 g (92%) of tert-butyl 3-bromophenyl-N-methylcarbamate are obtained.
With NaH; In water; ethyl acetate; N,N-dimethyl-formamide; (b) tert-butyl (3-bromophenyl)methylcarbamate 9.33 g (0.22 mol) of NaH at 60% in oil and 250 ml of DMF are introduced under nitrogen into a round-bottomed flask. 53 g (0.18 mol) of (3-bromophenyl)carbamic acid tert-butyl ester in solution in 150 ml of DMF are added dropwise. After 10 minutes, 14.5 ml (0.22 mmol) of methyl iodide are added dropwise. The mixture is stirred at room temperature for 30 minutes. After filtration of the NaI and evaporation of the DMF, the medium is solubilized in 350 ml of ethyl acetate and washed with twice 300 ml of water. After drying over sodium sulphate and evaporation of the solvents, 55 g (98%) of tert-butyl (3-bromophenyl)methylcarbamate are obtained in the form of a yellow liquid.
With sodium hydride; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; for 1h;Heating / reflux; A solution of 3-bromoaniline Compound 21a (2 mL, 18.4 mmol), di-tert-butyl dicarbonate (4. [05G,] 18.6 mmol) in THF (20 mL) was heated to reflux for 30 h under [N2.] The mixture was evaporated under reduced pressure, and the residue was dissolved in EtOAc. The solution was washed with saturated [NAHC03] solution and brine. The organic layer was dried over [MGS04,] filtered, and evaporated, to yield Compound 21b. MS (ES+) m/z [256. 8/258.] 8 [(M-CH3).] Sodium hydride (60% in oil; 0. [78G,] 19.5 mmol) was added in small portions to a solution of Compound 21b (4. [18G,] 15.4 mmol) and methyl iodide (1.21 mL, 19.5 mmol) in DMF [(50] mL) at [0 C.] The resulting mixture was allowed to warm to rt and stirred for 1 h. The mixture was poured in ice-water and extracted with EtOAc. The organic layer was separated, dried over [MGS04,] filtered, and evaporated under reduced pressure to yield Compound [21C.] MS, (ES+) m/z 270.9/272. 9 [(M-CH3).] [ ] Using the procedure described in Example 12 for converting Compound 12b to Compound 12d, Compound 21c was converted to Compound 21d. MS (ES+) m/z 455.0 [ (M+NA+).] Using the procedure described in Example 12 for converting Compound 12d to Compound 12e, Compound 21d was converted to Compound 21e. MS (ES+) m/z 510.9 [(M+NA+).] Using the procedure described in Example 12 for converting Compound 12e to Compound 12f, Compound [21E] was converted to Compound 21f. MS (ES+) m/z 512.8 (M+Na+). Using the procedure described in Example 12 for converting Compound 12f to Compound 12g, Compound 21f was converted to Compound 21g. MS (ES+) m/z 291.0 (M+H+). Using the procedure described in Example 12 for converting Compound 12g to Compound 12h, Compound 21g was converted to Compound 21h. MS (ES+) m/z 479.0 [(M+H+).] Using the procedure described in Example 12 for converting Compound 12h to Compound 11, Compound 21h was converted to Compound 79. MS (ES+) m/z 465.0 [(M+H HNMR (DMSO-D6,] 300 MHz) [8] 0.99 [(M,] 2H), 1.21 [(M,] 1H), 1.4-1. 65 [(M,] 3H), 1. [72] (m, 1H), 1.86 [(M',] 2H), 2.3-3. 0 (m, 13H), 3.17 (m, 1H), 3.42 (m, 2H), 3.87 (dd, J= =17. 7 Hz, [J =] 15.2 Hz, 1H), 4.40 (dd, J= 15.2 Hz, J= =11. 6 Hz, [1H),] 6.41 (d, J= [7.] 5 Hz, 1H), 7.1-7. 4 (m, [5H).]
General procedure: To a stirred solution of 8a (232 mg, 0.63 mmol) in DMF (7.0 mL) at 0C was added NaH (60%in mineral oil, 61.5 mg, 1.54 mmol) and the reaction mixture was allowed to warm up to RT over30 min. 6c (171 mg, 0.63 mmol) was added and the mixture was stirred for 2 hours. The reactionmixture was added dropwise into 2.0 M HCl (20 mL), extracted with DCM (30 mL × 3), and thecombined organic fractions were concentrated. Purification by silica gel chromatography(40%60% EtOAc/hexanes) afforded 9c (266 mg, 76%) as a white powder.

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YieldReaction ConditionsOperation in experiment
100% f-(3-bromophenyl)methylamine150 g (500 mmol) of tert-butyl (3-bromophenyl)-N-methylcarbamate are placed in 600 mL of dichloromethane and 383 mL (5 mol) of trifluoroacetic acid. The reaction medium is stirred at room temperature for 24 hours, and then treated with saturated aqueous sodium carbonate solution and extracted with dichloromethane. The organic phase is washed with water, dried over magnesium sulfate, filtered and evaporated. 99 g (100%) of (3-bromophenyl)methylamine are obtained.
100% 3-Bromophenyl)methylamine is prepared as follows:150 g (500 mmol) of tert-butyl (3-bromophenyl)-N-methylcarbamate are placed in 600 ml of dichloromethane and 383 ml (5 mol) of trifluoroacetic acid. The reaction medium is stirred at ambient temperature for 24 hours, then treated with a saturated aqueous sodium carbonate solution and extracted with dichloromethane. The organic phase is washed with water, dried over magnesium sulphate, filtered and evaporated. 99 g (100%) of (3-bromophenyl)methylamine are obtained.
90% Example 5Synthesis of (E)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl]-2-methylacrylic acid a-(3-bromophenyl)methylamine3.6 g (12.7 mmol) of tert-butyl 3-bromophenyl-N-methylcarbamate, prepared in a manner similar to that of Example 4b, are dissolved in 15 mL of dichloromethane. 5 mL of trifluoroacetic acid are added and the reaction mixture is stirred for 1 hour at room temperature. The reaction is worked up by addition of 50 mL of saturated sodium hydrogen carbonate solution and extraction with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then purified by chromatography on a column of silica eluted with a 50/50 heptane/ethyl acetate mixture. 2.14 g (90%) of (3-bromophenyl)methylamine are obtained in the form of an oil.
90% 5 ml_ of trifluoromethanesulfonic acid are added to a solution of 3.6 g (12.7 mmol) of (3- tert-butyl bromophenyl)-A/-methylcarbamate in 15 mL of dichloromethane. The reaction medium is stirred for 1 hour at room temperature (r.t.). The reaction is stopped by addition of 50 mL of saturated sodium hydrogen carbonate solution and then extracted with ethyl acetate. The solvents are evaporated off and the residue is then chromatographed on silica gel. Eluent (1/1 heptane/ethyl acetate). 2.14 g of oil are obtained. Yield 90%
90% c. (3-Bzomophenyl)methylamine; 5 ml of trifluoromethanesulfonic acid are added to a solution of 3.6 g (12.7 mmol) of tert-butyl (3-bromophenyl) -N-methylcarbamate in 15 mL of dichloromethane. The reaction medium is stirred for 1 hour at room temperature (RT) . The reaction is stopped by adding 50 ml of saturated sodium hydrogen carbonate solution and then extracted with ethyl acetate. The solvents are evaporated off and the residue is then chromatographed on silica gel, eluting with 1/1 heptane/ethyl acetate. 2.14 g of oil are obtained. 90% yield.
90% With trifluoroacetic acid; In dichloromethane; at 20℃; for 1h; 3.6 g (12.7 mmol) of tert-butyl (3-bromophenyl)-N-methylcarbamate, prepared in a manner analogous to Example 1b), are dissolved in 15 ml of dichloromethane. 5 ml of trifluoroacetic acid are added and the reaction mixture is stirred at ambient temperature for 1 hour. The reaction is halted by the addition of 50 ml of a saturated sodium hydrogen- carbonate solution and then extraction is carried out with ethyl acetate. The organic phases are combined and dried over sodium sulphate. The solvents are evaporated and then the residue is chromatographed on silica gel (heptane/ethyl acetate 50/50). 2.14 g of 3-bromo-N-methylaniline are obtained in the form of an oil. Yield = 90%.

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  • [ 561013-61-4 ]
YieldReaction ConditionsOperation in experiment
60% With potassium carbonate In water; toluene at 90℃; for 24h; 1.c 307 ml (615 mmol) of an aqueous potassium carbonate solution (2M) are added dropwise to a mixture of 61.5 g (205 mmol) of tert-butyl (3-bromobenzyl)-N- methylcarbamate, 46 g (307 mmol) of 4-formylbenzene- boronic acid and 500 ml of toluene. The reaction medium is subsequently degassed with argon and 7 g (6.2 mmol) of tetrakis(triphenylphosphine)palladium(0) are added. After heating at 90°C for 24 hours, the reaction medium is poured into water and extracted with ethyl acetate. The organic phase is separated by settling, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a silica column eluted with a mixture of heptane and ethyl acetate (70/30). After evaporating the solvents, 67 g of tert-butyl (4'-formylbiphenyl-3-yl)methylcarbamate are collected. Yield = 60%.
34.c (c) (c) tert-butyl (4'-formylbiphenyl-3-yl)methylcarbamate In a manner similar to Example 1(c), by reacting 55 g (0.19 mol) of tert-butyl (3-bromophenyl)methylcarbamate with 50.5 g (0.30 mol) of 4-formylbenzeneboronic acid, 48 g (80%) of tert-butyl (4'-formylbiphenyl-3-yl)methylcarbamate are obtained after purification by chromatography on a silica column eluted with a heptane and ethyl acetate (90/10) mixture.
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  • [ 24424-99-5 ]
  • [ 66584-32-5 ]
  • [ 57598-34-2 ]
YieldReaction ConditionsOperation in experiment
With dmap; triethylamine; In dichloromethane; at 20℃; for 24h; Step 1: tert-butyl N-(3-bromophenyl)-N-methyl-carbamate: To a solution of 3-bromo-N- methyl-aniline (4.00 g, 21.5 mmol) and Di-tert-butyl decarbonate (5.16 g, 23.6 mmol) in DCM was added triethylamine (12 mL, 86.0 mmol) and 4-dimethylaminopyridine (5.25 g, 4.3 mmol). The reaction mixture was stirred at room temperature for 24 h, then poured into water and extracted twice with ethyl acetate (ca.150 mL each). The organic layers were combined and washed with 0.5 N HCl, then brine, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. Purification by flash chromatography (elution with 0-10% v/v ethyl acetate in hexanes) afforded tert-butyl N-(3-bromophenyl)-N-methyl-carbamate.
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