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[ CAS No. 50371-52-3 ] {[proInfo.proName]}

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Chemical Structure| 50371-52-3
Chemical Structure| 50371-52-3
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CAS No. :50371-52-3 MDL No. :MFCD00662082
Formula : C6H2Br2Cl3NO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 370.25 Pubchem ID :-
Synonyms :

Safety of [ 50371-52-3 ]

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Application In Synthesis of [ 50371-52-3 ]

* 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.

  • Downstream synthetic route of [ 50371-52-3 ]

[ 50371-52-3 ] Synthesis Path-Downstream   1~22

  • 1
  • [ 5754-35-8 ]
  • [ 50371-52-3 ]
  • [ 154468-43-6 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; 4,5-Dibromo-N-[2-(1,3-dioxolan-2-yl)ethyl]pyrrole-2-carboxamide (11). A solution of <strong>[5754-35-8]2-(2-aminoethyl)-1,3-dioxolane</strong> (2.4 g, 20.6 mmol) and 4,5-dibromopyrrol-2-yl trichloromethyl ketone (7.6 g, 20.5 mmol) in 30 mL of acetonitrile was stirred at room temperature for 16 h. The reaction mixture was filtered and the precipitate 11 (6.8 g, 90%) was collected as a colorless solid: mp 155-157 C.; 1H NMR (CDCl3) d 1.99 (dt, 2H, J=6.0, 4.2), 3.61 (dt, 2H, J=6.0, 5.6), 3.92 (m, 2H), 4.05 (m, 2H), 5.00 (t, 1H, J=4.2), 6.51 (d, 1H, J=2.8), 6.66 (bs, 1H), 10.57 (bs, 1H); 13C NMR (CD3COCD3) d 34.3 (e), 35.5 (e), 65.4*2 (e), 99.4 (e), 103.4 (o), 105.4 (e), 113.0 (o), 129.1 (e), 160.0 (e); IR (nujol) 3358, 1646, 1569, 1412, 1372 cm-1; UV (CH3OH) 1max 275, 233, 214 (sh) nm; MS m/z (relative intensity) 371 (M++5, 50), 369 (M++3, 100), 367 (M++1, 50), 289 (13), 118 (25), 101 (50), 73 (30); Anal. Calcd for C8H10N2O2Br2: C, 32.63; H, 3.29; N, 7.61; Found: C, 32.77; H, 3.17; N, 7.51.
  • 2
  • [ 35302-72-8 ]
  • [ 72652-32-5 ]
  • [ 50371-52-3 ]
  • 3
  • [ 50371-52-3 ]
  • [ 13515-95-2 ]
  • (2S)-2-amino-6-[1-(4,5-dibromo-1H-pyrrol-2-yl-methanoyl)amino]hexanoic acid methyl ester [ No CAS ]
  • 4
  • [ 50371-52-3 ]
  • [ 290353-35-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 94 percent / dimethylformamide / 6 h 2: 84 percent / aq. 2N HCl / acetone / 8 h 3: 66 percent / p-toluene sulfonylchloride, Et3N / CH2Cl2 / 72 h
Multi-step reaction with 3 steps 1: 80 percent / acetonitrile / 24 h / 23 °C 2: 70 percent / TsOH / acetone; H2O / 12 h / Heating 3: 99 percent / CH3SO3H / 96 h / 45 °C
  • 5
  • [ 50371-52-3 ]
  • [ 15430-52-1 ]
  • [ 1006055-08-8 ]
  • 6
  • [ 50371-52-3 ]
  • [ 106092-09-5 ]
  • (S)-N-(2-amino-4,5,6,7-tetrahydrobenzo[1,2-d]thiazol-6-yl)-4,5-dibromo-1H-pyrrole-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% General procedure: A solution of (S)-4,5,6,7-tetrahydrobenzo[d]thiazol-2,6-amine(3) (1 mmol) and Na2CO3 (1 mmol) in DMF (10 ml) was stirred at room temperature for 15 min. 2,2,2-(Trichloroacetyl)pyrrole, 1-(4-bromo-1H-pyrrol-2-yl)-2,2,2-trichloroethanone or 2,2,2-trichloro-1-(4,5-dibromo-1H-pyrrol-2-yl)ethanone (1.1 mmol) was added and mixture was stirred at 40 C for 2.5 h. Solvent was removed under reduced pressure and purified by column chromatography with dichloromethane/methanol (20:1) as an eluent.
68% A solution of <strong>[106092-09-5](S)-4,5,6,7-tetrahydrobenzo[1,2-d]thiazole-2,6-diamine</strong> (0.200 g, 1.18 mmol) and Na2CO3 (1.18 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 15 min. Then 2,2,2-trichloro-1-(4,5-dibromo-1H-pyrrol-2-yl)ethan-1-one (0.438 g, 1.18 mmol) was added and the mixture stirred at 40 C for 2.5 h. Solvent was removed under reduced pressure and purified by column chromatography using dichloromethane/methanol (20:1) as eluent. Yield: 340 mg (68%); white crystals; mp 129-130C; [alpha]D -23.0 (c 0.18, MeOH); 1H NMR (400 MHz, DMSO-d6) delta 1.73-1.83 (m, 1H, HA-7), 1.89-1.96 (m, 1H, HB-7), 2.43-2.54 (m, 3H, signal overlapped with DMSO-d5, H-5, HA-4), 2.79 (dd, 1H, J = 5.5, 14.7 Hz, HB-4), 4.08-4.17 (m, 1H, CHNH), 6.69 (s, 2H, 2-NH2), 7.00 (s, 1H, Ar-H-3), 8.07 (d, 1H, J = 7.8 Hz, NH-C=O), 12.69 (s, 1H, Ar-NH) ppm; 13C NMR (101 MHz, DMSO-d6) delta 24.9, 28.7, 28.8, 45.5, 97.8, 104.5, 112.3, 112.9, 128.1, 144.2, 158.3, 166.2 ppm.
  • 7
  • [ 50371-52-3 ]
  • [ 2017-68-7 ]
  • [ 1569312-51-1 ]
YieldReaction ConditionsOperation in experiment
44% With triethylamine; In acetonitrile; at 60℃; for 24h; General procedure: 2,2,2-Trichloro-1-(4,5-dibromo-1H-pyrrol-2-yl)ethanone (3) (0.200 g, 0.54 mmol), and phenylmethanamine (0.058 g, 0.06 mL, 0.54 mmol) were dissolved in acetonitrile (10.0 mL). Triethylamine (5 equiv, 0.38 mL) was added to the solution, and the reaction mixture stirred at 60 C for 24 h. Solvent was removed from the reaction by rotary evaporation. The resulting yellow oil was purified using column chromatography from 2% MeOH/CH2Cl2 to afford N-benzyl-4,5-dibromo-1H-pyrrole-2-carboxamide (0.0978 g, 51%) as a brown solid, decomp. 125 C.
  • 8
  • [ 50371-52-3 ]
  • [ 3963-62-0 ]
  • [ 1569312-52-2 ]
YieldReaction ConditionsOperation in experiment
48% With triethylamine In acetonitrile at 60℃; for 24h; General procedure 2 General procedure: 2,2,2-Trichloro-1-(4,5-dibromo-1H-pyrrol-2-yl)ethanone (3) (0.200 g, 0.54 mmol), and phenylmethanamine (0.058 g, 0.06 mL, 0.54 mmol) were dissolved in acetonitrile (10.0 mL). Triethylamine (5 equiv, 0.38 mL) was added to the solution, and the reaction mixture stirred at 60 °C for 24 h. Solvent was removed from the reaction by rotary evaporation. The resulting yellow oil was purified using column chromatography from 2% MeOH/CH2Cl2 to afford N-benzyl-4,5-dibromo-1H-pyrrole-2-carboxamide (0.0978 g, 51%) as a brown solid, decomp. 125 °C.
  • 9
  • [ 50371-52-3 ]
  • [ 712-76-5 ]
  • [ 1569312-53-3 ]
YieldReaction ConditionsOperation in experiment
44% With triethylamine In acetonitrile at 60℃; for 24h; General procedure 2 General procedure: 2,2,2-Trichloro-1-(4,5-dibromo-1H-pyrrol-2-yl)ethanone (3) (0.200 g, 0.54 mmol), and phenylmethanamine (0.058 g, 0.06 mL, 0.54 mmol) were dissolved in acetonitrile (10.0 mL). Triethylamine (5 equiv, 0.38 mL) was added to the solution, and the reaction mixture stirred at 60 °C for 24 h. Solvent was removed from the reaction by rotary evaporation. The resulting yellow oil was purified using column chromatography from 2% MeOH/CH2Cl2 to afford N-benzyl-4,5-dibromo-1H-pyrrole-2-carboxamide (0.0978 g, 51%) as a brown solid, decomp. 125 °C.
  • 10
  • [ 50371-52-3 ]
  • [ 2258-21-1 ]
  • [ 1569312-55-5 ]
YieldReaction ConditionsOperation in experiment
13% With triethylamine In acetonitrile at 60℃; for 24h; General procedure 2 General procedure: 2,2,2-Trichloro-1-(4,5-dibromo-1H-pyrrol-2-yl)ethanone (3) (0.200 g, 0.54 mmol), and phenylmethanamine (0.058 g, 0.06 mL, 0.54 mmol) were dissolved in acetonitrile (10.0 mL). Triethylamine (5 equiv, 0.38 mL) was added to the solution, and the reaction mixture stirred at 60 °C for 24 h. Solvent was removed from the reaction by rotary evaporation. The resulting yellow oil was purified using column chromatography from 2% MeOH/CH2Cl2 to afford N-benzyl-4,5-dibromo-1H-pyrrole-2-carboxamide (0.0978 g, 51%) as a brown solid, decomp. 125 °C.
  • 11
  • [ 50371-52-3 ]
  • [ 56-92-8 ]
  • [ 292023-02-0 ]
YieldReaction ConditionsOperation in experiment
38% With piperidine; In N,N-dimethyl-formamide; at 150℃; for 0.0833333h;Microwave irradiation; 2,2,2-Trichloro-1-(4,5-dibromo-1H-pyrrol-2-yl)ethanone (3) (0.204 g, 0.54 mmol and histamine dihydrochloride (0.150 g, 0.81 mmol) were dissolved in N,N-dimethylformamide (4.0 mL). Piperidine (5 equiv, 0.27 mL) was added to the solution and the reaction mixture was subjected to microwave irradiation at 150 C for 5 min. Solvent was removed from the reaction by rotary evaporation. The resulting light brown oil was purified using column chromatography from 5% MeOH/CH2Cl2 to afford N-(2-(1H-imidazol-4-yl)ethyl)-4,5-dibromo-1H-pyrrole-2-carboxamide (0.076 g, 38%) as a light brown solid, decomp. 207 C. 1H NMR (DMSO-d6): delta 8.18 (t, J = 5.5 Hz, 1H), 7.53 (s, 1H), 6.89 (s, 1H), 6.80 (s, 1H), 3.42 (q, J = 6.8 Hz, 2H, obscured by water signal), 2.71 (t, J = 7.4 Hz, 2H). 13C NMR (DMSO-d6): delta 158.8, 134.7 (2 × C), 128.3, 116.7 (br), 112.4, 104.4, 97.7, 38.8, 27.1. HRMS (ESI) m/z: calculated for C10H9Br2N4O [M-H]- 358.9149; Found 358.9155.
  • 12
  • [ 50371-52-3 ]
  • [ 13214-66-9 ]
  • [ 1569312-45-3 ]
YieldReaction ConditionsOperation in experiment
63% With triethylamine In acetonitrile at 60℃; for 24h; General procedure 2 General procedure: 2,2,2-Trichloro-1-(4,5-dibromo-1H-pyrrol-2-yl)ethanone (3) (0.200 g, 0.54 mmol), and phenylmethanamine (0.058 g, 0.06 mL, 0.54 mmol) were dissolved in acetonitrile (10.0 mL). Triethylamine (5 equiv, 0.38 mL) was added to the solution, and the reaction mixture stirred at 60 °C for 24 h. Solvent was removed from the reaction by rotary evaporation. The resulting yellow oil was purified using column chromatography from 2% MeOH/CH2Cl2 to afford N-benzyl-4,5-dibromo-1H-pyrrole-2-carboxamide (0.0978 g, 51%) as a brown solid, decomp. 125 °C.
  • 13
  • [ 50371-52-3 ]
  • [ 106092-11-9 ]
  • (R)-N-(2-amino-4,5,6,7-tetrahydrobenzo[1,2-d]thiazol-6-yl)-4,5-dibromo-1H-pyrrole-2-carboxamide [ No CAS ]
  • 14
  • [ 131713-50-3 ]
  • [ 50371-52-3 ]
  • C10H14Br2N2O3 [ No CAS ]
  • 15
  • [ 50371-52-3 ]
  • [ 64987-16-2 ]
  • methyl 2-(2-(4,5-dibromo-1H-pyrrole-2-carboxamido)thiazol-4-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% A solution of 10 (1.044 g, 5.00 mmol) and Na2CO3 (0.530 g,5.00 mmol) in DMF (20 mL) was stirred at room temperature for 15 min. 2,2,2-Trichloro-1-(4,5-dibromo-1H-pyrrol-2-yl)ethan-1-one (1.852 g, 5.00 mmol) was added and mixture was stirred at 80 C overnight. Solvent was removed under reduced pressure, residue was suspended in ethyl acetate (60 mL) and successively washed with 10% citric acid (2 x 30 mL), saturated aqueous NaHCO3 solution (2 x 30 mL) and brine (30 mL), dried over Na2SO4, filtered and the solvent removed under reduced pressure. The crude product was recrystallized from methanol. Yield: 1.630 g (77.0%); white crystals; m.p. 200-202 C; IR (ATR) nu 3352, 3232, 3129, 2982, 1698, 1650, 1543, 1505, 1442, 1410, 1368, 1274,1218, 1172, 1116, 1085, 1010, 980, 886, 854, 823, 782, 729,687 cm-1; 1H NMR (400 MHz, DMSO-d6): delta 3.63 (s, 3H, CH3), 3.75 (s, 2H, CH2), 7.04 (s, 1H, thiazole-H), 7.45 (d, 1H, J = 2.6 Hz, pyrrole-H), 12.42 (s, 1H, NH), 13.12 (s, 1H, NH) ppm; 13C NMR (100 MHz, DMSO-d6): delta 36.4, 51.7, 98.8, 107.8, 110.8, 115.4, 125.8, 143.7, 156.6, 157.8, 170.5 ppm; HRMS (ESI-) m/z for C11H8N3O3SBr2 ([M-H]-): calcd 419.8653, found 419.8650; HPLC: method A, tr 13.09 min (95.4% at 254 nm).
77% A solution of <strong>[64987-16-2]methyl 2-(2-aminothiazol-4-yl)acetate</strong> (1.044 g, 5.00 mmol) and Na2CO3 (0.530 g, 5.00 mmol) in DMF (20 mL) was stirred at room temperature for 15 min. 2,2,2-Trichloro-1-(4,5-dibromo-1H-pyrrol-2-yl)ethan-1-one (1.852 g, 5.00 mmol) was added and mixture was stirred at 80 C overnight. Solvent was removed under reduced pressure, residue was suspended in ethyl acetate (60 mL) and successively washed with 10% citric acid (2 × 30 mL), saturated aqueous NaHCO3 solution (2 × 30 mL) and brine (30 mL), dried over Na2SO4, filtered and the solvent removed under reduced pressure. The crude product was recrystallized from methanol. Yield: 1.630 g (77.0%); white crystals; m.p. 200-202 C; 1H NMR (400 MHz, DMSO-d6): delta 3.63 (s, 3H, CH3), 3.75 (s, 2H, CH2), 7.04 (s, 1H, thiazole-H), 7.45 (d, 1H, J = 2.6 Hz, pyrrole-H), 12.42 (s, 1H, NH), 13.12 (s, 1H, NH) ppm; 13C NMR (100 MHz, DMSO-d6): delta 36.4, 51.7, 98.8, 107.8, 110.8, 115.4, 125.8, 143.7, 156.6, 157.8, 170.5 ppm.
  • 16
  • [ 50371-52-3 ]
  • [ 71-44-3 ]
  • N,N'-((butane-1'',4''-diylbis(azanediyl))bis(propane-3',1'-diyl))bis(4,5-dibromo-1H-pyrrole-2-carboxamide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With triethylamine; In tetrahydrofuran; at 20℃; for 18h;Inert atmosphere; General procedure: the coupling of substituted pyrroles with amine for synthesis of di-pyrroleanalogues 12-19.To a solution of pyrrole 2 (2 equiv.) in dry THF at r.t., under an atmosphere of nitrogen, amine(1 equiv.) and triethylamine (4 equiv.) were added dropwise. The mixture was stirred for 18-72 h and the solvent was removed in vacuo to give the crude product, which was purified as stated.
  • 17
  • [ 50371-52-3 ]
  • [ 22259-53-6 ]
  • N-((1H-indol-3-yl)methyl)-4,5-dibromo-1H-pyrrole-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 18h;Inert atmosphere; General procedure: This method was adapted from methods described by Richardset al.One equivalent of the appropriate 2,2,2-trichloroacetylpyrrolewas combined with 2 equivalents of the appropriate primary aminealong with 3 equivalents of anhydrous potassium carbonate and dissolvedin 4 mLs of anhydrous dimethylformamide (DMF) under argonand stirred for 18 h. The reaction was poured into 75 mLs EtOAc and25 mLs of deionized water, the aqueous layer was discarded and theorganic was further washed thrice with water, twice with 25 mLs 1 NHCl, and once with 25 mLs brine. The organic layer was then dried withanhydrous magnesium sulfate and evaporated under reduced pressure.The crude solid was purified by flash chromatography (5-20% EtOAc/Hexanes) to yield the final products.
  • 18
  • [ 21109-25-1 ]
  • [ 50371-52-3 ]
  • N-((1H-indol-2-yl)methyl)-4,5-dibromo-1H-pyrrole-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 18h;Inert atmosphere; General procedure: This method was adapted from methods described by Richardset al.One equivalent of the appropriate 2,2,2-trichloroacetylpyrrolewas combined with 2 equivalents of the appropriate primary aminealong with 3 equivalents of anhydrous potassium carbonate and dissolvedin 4 mLs of anhydrous dimethylformamide (DMF) under argonand stirred for 18 h. The reaction was poured into 75 mLs EtOAc and25 mLs of deionized water, the aqueous layer was discarded and theorganic was further washed thrice with water, twice with 25 mLs 1 NHCl, and once with 25 mLs brine. The organic layer was then dried withanhydrous magnesium sulfate and evaporated under reduced pressure.The crude solid was purified by flash chromatography (5-20% EtOAc/Hexanes) to yield the final products.
  • 19
  • [ 50371-52-3 ]
  • [ 3468-17-5 ]
  • N-((1H-indol-6-yl)methyl)-4,5-dibromo-1H-pyrrole-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With potassium carbonate; In N,N-dimethyl-formamide; at 20.0℃; for 18.0h;Inert atmosphere; General procedure: This method was adapted from methods described by Richardset al.One equivalent of the appropriate 2,2,2-trichloroacetylpyrrolewas combined with 2 equivalents of the appropriate primary aminealong with 3 equivalents of anhydrous potassium carbonate and dissolvedin 4 mLs of anhydrous dimethylformamide (DMF) under argonand stirred for 18 h. The reaction was poured into 75 mLs EtOAc and25 mLs of deionized water, the aqueous layer was discarded and theorganic was further washed thrice with water, twice with 25 mLs 1 NHCl, and once with 25 mLs brine. The organic layer was then dried withanhydrous magnesium sulfate and evaporated under reduced pressure.The crude solid was purified by flash chromatography (5-20% EtOAc/Hexanes) to yield the final products.
  • 20
  • [ 50371-52-3 ]
  • [ 66947-92-0 ]
  • methyl 2-(4,5-dibromo-1H-pyrrole-2-carboxamido)benzo[d]thiazole-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91.6% With sodium carbonate; In N,N-dimethyl-formamide; at 80℃; To a solution of <strong>[66947-92-0]methyl 2-aminobenzo[d]thiazole-6-carboxylate</strong> (500 mg, 2.40 mmol) in N,N- dimethylformamide Na2CO3 (255 mg, 2.40 mmol) and 2,2,2-trichloro-1-(4,5-dibromo-1H-pyrrole-2-yl)- ethan-1-one (0.968 g, 2.64 mmol) were added and the reaction mixture was stirred at 80 C overnight. The reaction mixture was cooled to room temperature, 10% citric acid aqueous solution was added and the mixture was cooled on ice bath. The precipitate that formed was filtered off and dried. Yield: 91.6% (1.01 g); light brown solid. (0399) 1H NMR (400 MHz, DMSO-d6) d 3.89 (s, 3H), 7.55 (d, J = 8.5 Hz, 1H), 7.81 (s, 1H), 8.04 (dd, J = 8.5, 1.8 Hz, 1H), 8.68 (d, J = 1.8 Hz, 1H), 12.84 (s, 1H), 13.30 (s, 1H). (0400) HRMS (ESI-) m/z for C14H8Br2N3O3S ([M-H]-): calculated 455.8653, found 455.8663.
  • 21
  • [ 50371-52-3 ]
  • [ 13531-52-7 ]
  • [ 2649465-50-7 ]
  • [ 2649465-51-8 ]
  • [ 2649465-52-9 ]
YieldReaction ConditionsOperation in experiment
1: 38% 2: 28% 3: 24% With triethylamine In tetrahydrofuran at 20℃; for 18h; Inert atmosphere; General Procedure A: General procedure: the coupling of substituted pyrroles with amine for synthesis of di-pyrroleanalogues 12-19.To a solution of pyrrole 2 (2 equiv.) in dry THF at r.t., under an atmosphere of nitrogen, amine(1 equiv.) and triethylamine (4 equiv.) were added dropwise. The mixture was stirred for 18-72 h and the solvent was removed in vacuo to give the crude product, which was purified as stated.
  • 22
  • [ 50371-52-3 ]
  • [ 124-20-9 ]
  • C17H21Br4N5O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With triethylamine In tetrahydrofuran at 20℃; for 48h; Inert atmosphere; General Procedure A: General procedure: the coupling of substituted pyrroles with amine for synthesis of di-pyrroleanalogues 12-19.To a solution of pyrrole 2 (2 equiv.) in dry THF at r.t., under an atmosphere of nitrogen, amine(1 equiv.) and triethylamine (4 equiv.) were added dropwise. The mixture was stirred for 18-72 h and the solvent was removed in vacuo to give the crude product, which was purified as stated.
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