1000573-99-8|4-Bromo-3-chloro-2-nitroaniline| Ambeed

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Quality Control of [ 1000573-99-8 ] Purity: 95% SDS Specification

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Product Details of [ 1000573-99-8 ]

CAS No. :	1000573-99-8
Formula :	C₆H₄BrClN₂O₂
M.W :	251.47
SMILES Code :	NC1=CC=C(Br)C(Cl)=C1[N+]([O-])=O
MDL No. :	MFCD09878187
InChI Key :	CQFJUGCVNFUHRZ-UHFFFAOYSA-N
Pubchem ID :	26599156

Safety of [ 1000573-99-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 1000573-99-8 ]

* 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 [ 1000573-99-8 ]

[ 1000573-99-8 ] Synthesis Path-Downstream 1~35

1
[ 59483-54-4 ]
[ 1000573-99-8 ]

Yield	Reaction Conditions	Operation in experiment
72%	With N-Bromosuccinimide; In acetic acid; for 0.75h;Reflux;	5.00 g (28.973 mmol) of 3-chloro-2-nitroaniline and 5.05 g (28.394 mmol) of N-bromosuccinimide were dissolved in 250 ml acetic acid. The mixture was boiled under reflux for 45 min. After cooling, the reaction mixture was added to 1.5 1 water. The resultant precipitate was filtered off and dried under high vacuum. We obtained 5.25 g (72% of theor.) of the target compound.LC-MS (method 9): R, = 2.16 min; MS (Elmin): m/z = 251 [M-H]+. 1H-NMR (400 MHz, DMSO-D6): δ [ppm] = 6.40 (sbr, 2H), 6.83 (d, IH), 7.56 (d, IH).
68.6%	With N-Bromosuccinimide; acetic acid; for 0.75h;Reflux;	4-Bromo-3-chloro-2-nitroaniline3-Chloro-2-nitroaniline (10 g, 57.9 mmol) and NBS (10.31 g, 57.9 mmol) were dissolved in AcOH (500 mL). The reaction mixture was stirred at reflux temperature for 45 min. After cooling, the reaction mixture was added to 1.5L of water. The resultant precipitate was filtered off and dried under high vacuum to give 10 g (68.6%) of the title compound.
67%	With N-Bromosuccinimide; acetic acid; for 1h;Reflux;	Intermediate 12A; 4-bromo-3-chloro-2-nitroaniline; 3-Chloro-2-nitroaniline (5.00 g, 29.0 mmol) was dissolved in glacial acetic acid (258 mL). N-Bromosuccinimide (5.06 g, 28.4 mmol) was added and the resulting mixture was refluxed for 1 hour. The reaction was cooled to room temperature and poured into water to give a precipitate that was filtered, rinsed with water and dried to constant weight to give the title compound (4.78 g, 67%o). .H NMR (400 MHz, CDCL3) δ ppm 7.46 (d, J= 9.0, 1H), 6.64 (d, J= 9.0, 1H), 4.74 (s, 2H).

62%	With N-Bromosuccinimide; acetic acid;Inert atmosphere; Reflux;	A solution of 3-chloro-2-nitroaniline (25.0 g 0.145 mol) and NBS (25.8 g 0.145 mol) in acetic acid (1 L) was heated at reflux under N2 overnight. Water (1 L) was added and the insoluble matter was collected by filtration to give the title compound (22.3 g, 62%) as a gray solid. LCMS-C (ES-API): rt 3.84 min; m/z 250.9, 252.9 [M+H]+. 1 H NMR (400 MHz, DMSO-de) d 7.56 (d, J = 9.2 Hz, 1 H), 6.84 (d, J = 9.2 Hz, 1 H), 6.41 (s, 2H).
23%	With N-Bromosuccinimide; acetic acid; at 80℃; for 1.5h;	In a 2 L three necked flask, a solution of 3-chloro-2-nitroaniline (60 g, 348 mmol) in AcOH (600 mL) was treated portionwise with NBS (61.9 g, 348 mmol). The resultant orange solution was heated at 80 C for 1.5 h. The reaction mixture was cooled to RT and was poured into stirred ice water (800 mL). The resultant orange precipitate was collected by filtration, washed with water (200 mL). The orange residue was collected and dissolved in EtOAc (500 mL). The solution was dried with MgSO4, filtered and the solvent was concentrated in vacuo to give an orange solid (86.5 g). The residue was recrystallised from 10% EtOAc/iso-Hexane (500 mL). The resultant solid was filtered, rinsing with iso-Hexane (100 mL), and dried in vacuo to afford a light orange solid (39.88 g, 158.6 mmol, 46%). The filtrate was concentrated in vacuo to give an orange solid. The residue was recrystallised from 10% Ac/iso-Hexane (250 mL). The resultant solid was filtered, rinsing with iso-Hexane (50 mL), and dried in vacuo to afford a light orange solid (20 g, 79.53 mmol, 23%).1H NMR in DMSO-d6: (7.55 (1H, d), 6.84 (1H, d), 6.40 (2H, s). Step
13g	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20℃;Inert atmosphere;	A solution of BS (10.31 g ) in DMF (25 mL) was added to a solution of 3- chloro-2-nitroaniline in DMF (100 mL) at 0 C. The resulting solution was stirred at 0 C for 1 hour then allowed to warm to room temperature and stirred at room temperature overnight. The orange solution was taken up in EtOAc and washed 3 times with water. Then the organic layer was dried (Na2S04) and the solvent was removed under reduced pressure. The residue was rinsed with hexanes and collected via filtration to provide 13 g of the title compound as a brown solid.
13 g	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20℃;	[0658] A solution ofNBS (10.31 g ) in DMF (25 mL) was added to a solution of 3-chloro- 2-nitroaniline in DMF (100 mL) at 0 C. The resulting solution was stirred at 0 C for 1 h, then allowed to warm to room temperature and stirred overnight. The orange solution was taken up in EtOAc and washed 3 times with water. Then the organic layer was dried (Na2SO4) and the solvent was removed under reduced pressure. The residue was rinsed with hexanes and collected via filtration to provide 13 g of brown solid.

References: [1]Patent: WO2010/20363,2010,A1 .Location in patent: Page/Page column 84.
[2]Patent: WO2015/92713,2015,A1 .Location in patent: Page/Page column 273; 274.
[3]Patent: WO2012/83170,2012,A1 .Location in patent: Page/Page column 155.
[4]Patent: WO2021/9362,2021,A1 .Location in patent: Page/Page column 94.
[5]Patent: WO2021/33153,2021,A1 .Location in patent: Page/Page column 118.
[6]Patent: WO2017/35408,2017,A1 .Location in patent: Paragraph 0628.
[7]Patent: WO2017/35360,2017,A1 .Location in patent: Paragraph 0658.

2
[ 1000573-99-8 ]
[ 1008361-80-5 ]

Yield	Reaction Conditions	Operation in experiment
79%		Intermediate 12B; 4-bromo-3-chlorobenzene-l,2-diamine; 4-Bromo-3-chloro-2-nitroaniline (4.78 g, 19.01 mmol) was dissolved in ethanol (112 mL). Tin (II) chloride (14.42 g, 76 mmol) was added, and the resulting mixture was stirred at reflux for 12 hours. The mixture was cooled to room temperature, poured into water, and adjusted to pH 5 with saturated sodium bicarbonate solution. The resulting solid was filtered and rinsed well with ethyl acetate. The filtrate was washed with water and brine, dried over Na2SOt, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using a solvent gradient of 0-50% EtOAc in hexane to give the title compound (3.32 g, 79%). .H NMR (400 MHz, CDC13) δ ppm 6.94 (d, 1H), 6.51 (d, J= 7.0, 1H), 3.87 (br s, 2H), 3.46 (br s, 2H). I
70%	With tin(ll) chloride; In ethanol; at 70℃;	5.25 g (20.877 mmol) of the compound from example 43A was dissolved in 120 ml ethanol and 18.84 g (83.508 mmol) of tin(II) chloride dihydrate was added. The mixture was stirred overnight at 700C. After cooling, water was added, it was made weakly alkaline with saturated aqueous sodium hydrogen carbonate solution and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in a rotary evaporator at reduced pressure. The residue was dried under high vacuum. We obtained 4.40 g (purity 74%, 70% of theor.) of the target compound.LC-MS (method 3): R, = 1.42 min; MS (EIpos): m/z = 221 [M+H]+.
6.7g	With tin(II) chloride dihdyrate; In ethanol; for 4h;Reflux; Inert atmosphere;	A mixture of 10 g of <strong>[1000573-99-8]4-bromo-3-chloro-2-nitroaniline</strong> and 36 g of SnCl2.2H20 in EtOH (150 mL) was heated at reflux for 4 hours. The reaction mixture was allowed to cool, then was quenched carefully with sat. aq. NaHCCb solution until slightly basic. The thick mixture was extracted with EtOAc. Dried (Na2S04), concentrated and purified by column chromatography (silica gel, 0-40 % EtOAc in hexanes) to afford 6.7 g of 4-bromo-3-chlorobenzene-l,2-diamine as a tan solid.

6.7 g

With tin(II) chloride dihdyrate; In ethanol; for 4h;Reflux;

[0659] A mixture of 10 g of <strong>[1000573-99-8]4-bromo-3-chloro-2-nitroaniline</strong> and 36 g of SnC12.2H20 in EtOH (150 mL) was heated at reflux for 4 h. The reaction mixture was allowed to cool and was then quenched carefully with saturated aqeuous NaHCO3 solution until slightly basic. The thick mixture was extracted with EtOAc, dried withNa2SO4, concentrated, and purified by ISCO (0-40 % EtOAc in Hexanes) to afford 6.7 g of the title compound as tan solid.

References: [1]Patent: WO2012/83170,2012,A1 .Location in patent: Page/Page column 155.
[2]Patent: WO2010/20363,2010,A1 .Location in patent: Page/Page column 84.
[3]Patent: WO2017/35408,2017,A1 .Location in patent: Paragraph 0629.
[4]Patent: WO2017/35360,2017,A1 .Location in patent: Paragraph 0659.

3
[ 1000573-99-8 ]
[ 1357159-33-1 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1261 - 1273.

4
[ 1000573-99-8 ]
[ 1357159-34-2 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1261 - 1273.

5
[ 1000573-99-8 ]
[ 1357158-78-1 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1261 - 1273.

6
[ 1000573-99-8 ]
C₂₉H₃₁N₃O₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1261 - 1273.

7
[ 1000573-99-8 ]
[ 1357159-32-0 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1261 - 1273.
[2]Patent: WO2015/92713,2015,A1 .

8
[ 1000573-99-8 ]
[ 77-78-1 ]
[ 1357159-31-9 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1261 - 1273.

9
[ 1000573-99-8 ]
5-bromo-4-chlorobenzo[c][1,2,5]oxadiazole 1-oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium hydroxide; In ethanol;	Preparation 33 5-Bromo-4-chlorobenzo[c][1,2,5]oxadiazole 1-oxide 4-Bromo-3-chloro-2-nitroaniline (4.1 g, 16 mmol) was dissolved in 60 mL ethanol, treated with 45% potassium hydroxide solution (2.0 g, 16 mmol), cooled to -5 to 0 C. and treated drop wise with commercial bleach solution (32 mL, 6 wt. %, 31 mmol) over 20 min. The mixture was stirred for 90 min at 0-15 C. and poured into 700 mL water. The precipitated product was collected by filtration, washed well with water and then dried under vacuum at 80 C. to give the title compound (3.2 g, 81%): EIMS m/z 248.

References: [1]Patent: US2014/274702,2014,A1 .Location in patent: Page/Page column.

10
[ 1000573-99-8 ]
5-Bromo-4-chlorobenzo[c][1,2,5]oxadiazole [ No CAS ]

References: [1]Patent: US2014/274702,2014,A1 .

11
[ 1000573-99-8 ]
3-(4-chloro-1-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-3-(4-methyl-3-(((R)-4-methyl-1,1-dioxido-3,4-dihydro-2H-benzo[b][1,4,5]oxathiazepin-2-yl)methyl)phenyl)propanoic acid [ No CAS ]

References: [1]Patent: WO2015/92713,2015,A1 .

12
[ 1000573-99-8 ]
5-bromo-4-chloro-1-methyl-1H-benzo[d][1,2,3]triazole [ No CAS ]

References: [1]Patent: WO2015/92713,2015,A1 .

13
[ 1000573-99-8 ]
(E)-ethyl 3-(4-chloro-1-methyl-1H-benzo[d][1,2,3]triazol-5-yl)acrylate [ No CAS ]

References: [1]Patent: WO2015/92713,2015,A1 .

14
[ 1000573-99-8 ]
ethyl 3-(4-chloro-1-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-3-(3-(hydroxymethyl)-4-methylphenyl)propanoate [ No CAS ]

References: [1]Patent: WO2015/92713,2015,A1 .

15
[ 1000573-99-8 ]
ethyl 3-(4-chloro-1-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-3-(4-methyl-3-(((R)-4-methyl-1,1-dioxido-3,4-dihydro-2H-benzo[b][1,4,5]oxathiazepin-2-yl)methyl)phenyl)propanoate [ No CAS ]

References: [1]Patent: WO2015/92713,2015,A1 .

16
[ 1000573-99-8 ]
[ 74-88-4 ]
[ 1357159-31-9 ]

Yield	Reaction Conditions	Operation in experiment
56.8%		4-Bromo-3-chloro-N-methyl-2-nitroanilineTo a solution of the <strong>[1000573-99-8]4-bromo-3-chloro-2-nitroaniline</strong> (10 g, 39.8 mmol) in DMF (300 mL) at 0 C, NaH (1.145 g, 47.7 mmol) was added. After stirring for 30 min, Mel (2.98 mL, 47.7 mmol) was added and the reaction mixture was stirred 30 min further. Water (10 mL) was added. The red precipitate was collected by filtration, washed with water and dried to give 6 g (56.8%) of the title compound.

References: [1]Patent: WO2015/92713,2015,A1 .Location in patent: Page/Page column 274.

17
[ 4771-47-5 ]
[ 1000573-99-8 ]

References: [1]Patent: WO2015/92713,2015,A1 .

18
[ 1000573-99-8 ]
methyl 4-chloro-1-(cyclopropylmethyl)-2-(9-ethyl-9H-carbazol-3-yl)-1H-benzimidazole-5-carboxylate [ No CAS ]

References: [1]Patent: JP2016/501241,2016,A .

19
[ 1000573-99-8 ]
4-chloro-1-(cyclopropylmethyl)-2-(9-ethyl-9H-carbazol-3-yl)-1H-benzimidazole-5-carboxylic acid [ No CAS ]

References: [1]Patent: JP2016/501241,2016,A .

20
[ 1000573-99-8 ]
4-bromo-3-chloro-1-N-(cyclopropylmethyl)benzene-1,2-diamine [ No CAS ]

References: [1]Patent: JP2016/501241,2016,A .

21
[ 1000573-99-8 ]
3-[5-bromo-4-chloro-1-(cyclopropylmethyl)-1H-benzimidazole 2-yl]-9-ethyl-9H-carbazole [ No CAS ]

References: [1]Patent: JP2016/501241,2016,A .

22
[ 1000573-99-8 ]
[ 1489-69-6 ]
4-bromo-3-chloro-N-(cyclopropylmethyl)-2-nitroaniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		In addition 650mg of 4-bromo-3-chloro-2-nitro aniline (2.59mmol) in trifluoroacetic acid 5ml, was cooled to -15 , the process is divided in triacetoxy sodium hydrosulfite boric acid of 822mg (3.88mmol) then, the mixture was stirred at -15 10 minutes. Then added cyclopropane carbaldehyde in 272mg of dichloromethane 5 ml (3.88 mmol), additional 30 min, and stirred at -15 C.. Subsequently, the reaction mixture was poured into cold saturated sodium bicarbonate solution and extracted three times with dichloromethane. The organic phase was filtered and concentrated. Thus, to give the title compound 720mg (87%).

References: [1]Patent: JP2016/501241,2016,A .Location in patent: Paragraph 0163.

23
[ 1000573-99-8 ]
7-bromo-8-chloro-1,2,3,4-tetrahydroquinoxalin-2-one [ No CAS ]

References: [1]Patent: WO2017/35408,2017,A1 .
[2]Patent: WO2021/33153,2021,A1 .

24
[ 1000573-99-8 ]
1-(2-((2S,4R)-2-((3-(5-chloro-3-oxo-1,2,3,4-tetrahydroquinoxalin-6-yl)-2-fluorophenyl)carbamoyl)-4-fluoropyrrolidin-1-yl)-2-oxoethyl)-1H-indazole-3-carboxamide [ No CAS ]