[ CAS No. 120781-02-4 ] {[proInfo.proName]}

Name: 120781-02-4|Methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylate|95%
Brand: Ambeed
SKU: A270639
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Quality Control of [ 120781-02-4 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 120781-02-4 ]

CAS No. :	120781-02-4	MDL No. :	MFCD02179563
Formula :	C₆H₇BrN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZTQDLPCCSZIZFV-UHFFFAOYSA-N
M.W :	219.04	Pubchem ID :	26343677
Synonyms :

Safety of [ 120781-02-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 120781-02-4 ]

* 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.

Upstream synthesis route of [ 120781-02-4 ]
Downstream synthetic route of [ 120781-02-4 ]

[ 120781-02-4 ] Synthesis Path-Upstream 1~4

1
[ 17289-20-2 ]
[ 120781-02-4 ]

Reference： [1] Synthesis, 1988, # 10, p. 767 - 771
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 12, p. 5086 - 5098
[3] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 18, p. 4984 - 4995

2
[ 41806-40-0 ]
[ 120781-02-4 ]

Reference： [1] Synthesis, 1988, # 10, p. 767 - 771

3
[ 19485-38-2 ]
[ 120781-02-4 ]

Reference： [1] Synthesis, 1988, # 10, p. 767 - 771

4
[ 19485-35-9 ]
[ 120781-02-4 ]

Reference： [1] Synthesis, 1988, # 10, p. 767 - 771

[ 120781-02-4 ] Synthesis Path-Downstream 1~47

1
[ 17289-20-2 ]
[ 120781-02-4 ]

Yield	Reaction Conditions	Operation in experiment
27%		To the solution of commercially available 4.3 g methyl 3-methylimidazole-4-carboxyIate in 100 mL THF at 23 C was added 7.4 g lithium tertbutoxide and reaction mixture was stirred at 23 C for 15 min. Then, 10.9 g N-bromosuccinimide (NBS) was added and reaction mixture was stirred at 23 C for additional 12 h. Reaction mixture was quenched with water and was basified with sat. NaHCC>3 solution to pH 14. The compound was extracted with EtOAc (20 mL x 3), combined organic layer was dried over Na2S04and concentrated under reduced pressure to get crude compound which was purified by column chromatography over silica gel using 30 % EtOAc in />heptane as an eluent to afford the title compound as off white solid (1.8 g; 27.0% yield).

Reference： [1]Synthesis,1988,p. 767 - 771
[2]Journal of Medicinal Chemistry,2017,vol. 60,p. 5086 - 5098
[3]Patent: WO2019/137995,2019,A1 .Location in patent: Page/Page column 125
[4]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 4984 - 4995

2
[ 41806-40-0 ]
[ 120781-02-4 ]

Reference： [1]Synthesis,1988,p. 767 - 771

3
[ 19485-38-2 ]
[ 120781-02-4 ]

Reference： [1]Synthesis,1988,p. 767 - 771

4
[ 19485-35-9 ]
[ 120781-02-4 ]

Reference： [1]Synthesis,1988,p. 767 - 771

6
[ 120781-02-4 ]
[ 852180-96-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With water; sodium hydroxide; In ethanol; at 20℃; for 1h;	1 g (4.565 mmol) of methyl 1-methyl-2-bromoimi- dazole-5-carboxylate (Vu-i) was dissolved in 10 ml of ethanol, 5.48 ml of iN NaOH (aq.) was added and the mixture was stirred at room temperature for 60 mm. After addition of 5.5 ml of iN HC1 (aq.) (adjusted to pH .-3), a white precipitate is formed. The mixture was concentrated to dryness and, in an ultrasonic bath, suspended in 6 ml of watet The white crystals were filtered oil and washed with 2 ml of water. The mother liquor was concentrated almost to dryness. The crystals were filtered off with suction and washed with a little watet The combined crystals were dried under oil pump vacuum. Yield: 890 mg (95% of theory).log P[a]: 0.31; ?H-NMR (d5-DMSO, 400 MHz); oe=3.82 (s, 3H),7.60 (s, 1H), 13.15 (s, 1H) ppm.
95%	With water; sodium hydroxide; In ethanol; at 20℃; for 1h;	1 g (4.565 mmol) of <strong>[120781-02-4]methyl 1-methyl-2-bromoimidazole-5-carboxylate</strong> (ABCR) was dissolved in 10 ml of ethanol, 5.48 ml of 1 N NaOH(aq.) were added and the mixture was stirred at room temperature for 60 min. After addition of 5.5 ml of 1N HCl(aq.) (adjusted to pH 3), a white precipitate is formed. The mixture was concentrated to dryness and, in an ultrasonic bath, suspended in 6 ml of water. The white crystals were filtered off and washed with 2 ml of water. The mother liquor was concentrated almost to dryness. The crystals were filtered off with suction and washed with a little water. The combined crystals were dried under oil pump vacuum. Yield: 890 mg (95% of theory). (0486) log P[a]: 0.31; (0487) 1H-NMR (d6-DMSO, 400 MHz); delta=3.82 (s, 3H), 7.60 (s, 1H), 13.15 (s, 1H) ppm.
89%	With water; lithium hydroxide; In tetrahydrofuran; methanol; at 0℃; for 1h;	To the solution of 1.8 g methyl 2-bromo-3-methyl-imidazole-4-carboxylate in mixture ofTHF:MeOH (20 ml_ : 20 mL) at 0C was added a solution of 0.7 g LiOH in H20 (20 mL). After the addition was completed reaction mixture was stirred at 0C for 1 h. Reaction mixture was concentrated under reduced pressure and was diluted with 20 mL of water, acidified with solid KHSO4 and compound was extracted with EtOAc (20 ml x 2). The combined organic layer was washed with brine, dried over Na2S04and concentrated under reduced pressure to afford the title compound as colorless oil (1.5 g, 89.0% yield).1H NMR (400 MHz DMSO-d6): d 7.61 (s, 1 H), 3.82 (s, 3 H).

82%

With lithium hydroxide; water; In tetrahydrofuran; at 20℃; for 2.5h;

To a suspension of <strong>[120781-02-4]methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylate</strong> (2.18 g, 10 mmol) in tetrahydrofuran (60 mL) and water (6 mL) was added lithium hydroxide (0.72 mg, 30 mmol) and the reaction mixture was allowed to stir at room temperature for 2.5 h. The solvent was removed under reduced pressure and water was added followed by formic acid, the resulting precipitate was filtered, washed with water and dried under vacuum overnight to afford the 2-bromo-1-methyl-1H-imidazole-5-carboxylic acid (82%). 1H-NMR (300 MHz, CDCl3): 7.79 (s, 1H), 3.91 (s, 3H). LCMS (ESI+) 205.0 (MH+).

Reference： [1]Patent: US2018/7900,2018,A1 .Location in patent: Paragraph 0413; 0414; 0415; 0416
[2]Patent: US2019/47982,2019,A1 .Location in patent: Paragraph 0483-0487
[3]Patent: WO2019/137995,2019,A1 .Location in patent: Page/Page column 126
[4]Patent: US2009/23707,2009,A1 .Location in patent: Page/Page column 41
[5]ChemMedChem,2019,vol. 14,p. 1701 - 1709

7
[ 461702-08-9 ]
[ 120781-02-4 ]
[ 1104736-12-0 ]

Yield	Reaction Conditions	Operation in experiment
40%	With caesium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 80℃; for 7h;	To a solution of 1-[4-(4,4,5,5-tetramethyl)-[1,3,2]-dioxaborolan-2-yl]-benzyl-1H-benzoimidazole (0.527 g, 1.5 mmol) and <strong>[120781-02-4]2-bromo-3-methyl-3H-imidazole-4-carboxylic acid methyl ester</strong> (Anichem LLC, 0.328 g, 1.5 mmol) in anhydrous DMF (5 mL) under nitrogen was added Pd(dppf)2Cl2 (53 mg, 0.065 mmol) and cesium carbonate (0.786 g, 2.4 mmol) and the reaction mixture was heated to 80 C. and allowed to stir for 7 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and the solids filtered off. The filtrate was washed with water, dried (Na2SO4) and the solvent removed under reduced pressure. Purification by flash chromatography (silica, dichloromethane/methanol 99: 1?97:3) provided the title compound (40%). LCMS (ESI+) 347.2 (MH+).

Reference： [1]Patent: US2009/23707,2009,A1 .Location in patent: Page/Page column 39-40

8
[ 1104736-29-9 ]
C₁₃H₁₁BN₂O₂ [ No CAS ]
[ 120781-02-4 ]
[ 1104736-30-2 ]

Yield	Reaction Conditions	Operation in experiment
36%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 90℃; for 12h;	To a solution of 1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-benzoimidazole (0.43 g, 1.5 mmol) and <strong>[120781-02-4]2-bromo-3-methyl-3H-imidazole-4-carboxylic acid methyl ester</strong> (0.25 g, 1.15 mmol) in DME (9 mL) was added tetrakis(triphenylphosphine)palladium(0) (0.07 g, 0.057 mmol) and 2 M aqueous potassium carbonate (1.4 mL) and the reaction mixture was heated at 90 C. for 12 h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate. The reaction mixture was filtered and the filtrate washed with water, dried (Na2SO4), and the solvent removed under reduced pressure. Purification by flash column chromatography (silica, petroleum ether:ethyl acetate 7:3?1:1 then dichloromethane:methanol 99:1?97:3) provided the title compound (36%). LCMS (ESI+) 332.2 (MH+).

Reference： [1]Patent: US2009/23707,2009,A1 .Location in patent: Page/Page column 42-44

9
[ 1765-93-1 ]
[ 120781-02-4 ]
[ 1202942-04-8 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 855 - 866

10
[ 128796-39-4 ]
[ 120781-02-4 ]
[ 1202942-02-6 ]

Yield	Reaction Conditions	Operation in experiment
980 mg	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; water; at 120℃; for 0.5h;Microwave irradiation;	(1) 2-bromo-3-methyl -3H- to imidazole-4-carboxylic acid methyl ester (800mg) 4-(trifluoromethyl)benzeneboronic acid(1.04g), tetrakis(triphenylphosphine)palladium(422mg) And as a solvent was stirred in tetrahydrofuran (9), saturated sodium carbonate (3), was added water (1.5), and microwave irradiation for 30 minutes at 120 . After the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The resulting residue was purified by silica gel column chromatography (n- hexane: ethyl acetate) [(trifluoromethyl) 4-phenyl] After purification, 3-methyl-2--3H- imidazole-4-carboxylic acid methyl ester ( It was obtained 980mg) as a yellow solid.

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 855 - 866
[2]Patent: KR2015/2661,2015,A .Location in patent: Paragraph 0393; 0394

11
[ 120781-02-4 ]
[ 126747-14-6 ]
[ 1202942-03-7 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 855 - 866

12
[ 120781-02-4 ]
[ 149507-26-6 ]
[ 1202942-06-0 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 855 - 866

13
[ 120781-02-4 ]
[ 139301-27-2 ]
[ 1202942-05-9 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 855 - 866

14
[ 120781-02-4 ]
[ 652148-92-0 ]
[ 1398414-77-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 120℃; for 0.666667h;	Bromide 22-83 (1.00 g, 4.56 mmol) is combined with boronate 16-61 (1.30 g, 5.43 mmol), Pd(PPh3)4 (275 mg, 0.238 mmol), and aqueous Na2C03 solution (5.0 mL, 2.0 M, 10.0 mmol) in 1,2-DME (15 mL). The mixture is irradiated at 120 C for 40 min, then cooled to room temperature and concentrated under a stream of N2. The crude material is purified by column chromatography on C18 silica (using a solvent gradient of 5-75% MeCN:H20 + 0.1% TFA) to afford intermediate 22-84 (370 mg).

Reference： [1]Patent: WO2012/122340,2012,A1 .Location in patent: Page/Page column 74

15
[ 120781-02-4 ]
[ 98-80-6 ]
[ 746671-40-9 ]

Yield	Reaction Conditions	Operation in experiment
81%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In ethanol; toluene; at 100℃; for 1h;Inert atmosphere;	Methyl-2-bromo-1-methyl-1H-imidazole-5-carboxylate (1 g, 4.56 mmol) and phenylboronic acid (0.67 g, 5.48 mmol) were dissolved in toluene-EtOH (80 mL, 5:3 v/v) and the solution was purged with argon for 10 min. K2CO3 (10 mL, 2M solution) and catalytic PdCl2(dppf) (82 mg, 0.12 mmol) were added and the reaction mixture was heated to 100 C for 1 h. The reaction mixture was then cooled to room temperature and concentrated under reduced pressure. The residue was diluted with water and washed with EtOAc. The aqueous layer was acidified to pH ?6 using 1.5N HCl and the crude product was extracted with EtOAc. The combined extracts were dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica 60-120 mesh, eluent 35-45% EtOAc in petroleum ether) to get methyl 1-methyl-2-phenyl-1H-imidazole-5-carboxylate (800 mg, yield 81%) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) delta 7.86 (s, 1 H), 7.63 - 7.61 (m, 2H), 7.51 - 7.48 (m, 3H), 3.96 (s, 3H), 3.89 (s, 3H). MS (ESI) m/z: Calculated for C12H12N2O2: 216.09; found: 2168.8 (M+H)+.

Reference： [1]Patent: EP2533783,2015,B1 .Location in patent: Paragraph 0775-0776
[2]Journal of Medicinal Chemistry,2017,vol. 60,p. 5086 - 5098

16
N,N-bis(4-methoxybenzyl)-4-((3-phenyl-1H-pyrazol-4-yl)methyl)benzenesulfonamide [ No CAS ]
[ 120781-02-4 ]
methyl 2-(4-(4-(N,N-bis(4-methoxybenzyl)sulfamoyl)benzyl)-3-phenyl-1H-pyrazol-1-yl)-1-methyl-1H-imidazole-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33.0%	With potassium phosphate; copper(l) iodide; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane; In toluene; at 110℃;Inert atmosphere;	[0277] In a microwave tube was placed N,N-bis(4-methoxybenzyl)-4-((3-phenyl-1H- pyrazol-4-yl)methyl)benzenesulfonamide (138 mg, 0.25 mmol), methyl 2-bromo-i-methyl- 1 H-imidazole-5-carboxylate (54.8 mg, 0.25 mmol), (1 S,2S)-Ni ,N2-dimethylcyclohexane- 1,2- diamine (14.22 mg, 0.100 mmol), Cul (9.52 mg, 0.050 mmol), and Phosphoric acid, potassium salt (159 mg, 0.750 mmol). The air was removed and re-filled with N2 (3 times). Then Toluene (2 ml) was added and the mixture was stirred at 110 C for overnight. After cooling to rt, the mixture was dilute with EtOAc (3 mL) and filtered through celite and eluted with EtOAc. The filtrate was concentrated and the mixture was purified by silica gel chromatography using 10-25% EtOAc/hexane as the eluent to give methyl 2-(4-(4-(N,N- bis(4-methoxybenzyl)sulfamoyl)benzyl)-3 -phenyl- 1 H-pyrazol- 1 -yl)- i-methyl- 1H-imidazole- 5-carboxylate (57 mg, 0.082 mmol, 33.0 % yield). MS (M+H) = 692.

Reference： [1]Patent: WO2016/109559,2016,A2 .Location in patent: Paragraph 0276; 0277

17
N,N-bis(4-methoxybenzyl)-4-((3-phenyl-1H-pyrazol-4-yl)methyl)benzenesulfonamide [ No CAS ]
[ 120781-02-4 ]
1-methyl-2-(3-phenyl-4-(4-sulfamoylbenzyl)-1H-pyrazol-1-yl)-1H-imidazole-5-carboxylic acid trifluoroacetate [ No CAS ]

Reference： [1]Patent: WO2016/109559,2016,A2

18
[ 128796-39-4 ]
[ 120781-02-4 ]
[ 1373150-44-7 ]

Reference： [1]Patent: KR2015/2661,2015,A

19
[ 120781-02-4 ]
5-((1H-imidazol-1-yl)methyl)-1-methyl-2-phenyl-1H-imidazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 5086 - 5098

20
[ 120781-02-4 ]
[ 161670-81-1 ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 5086 - 5098

21
[ 120781-02-4 ]
[ 22325-27-5 ]
C₁₂H₁₄N₄O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17.3%	With copper(I) oxide; In N,N-dimethyl-formamide;Inert atmosphere; Reflux;	Under argon, 0.7 g (5 mmol) of 2-mercapto-4,6- dimethylpyrimidine, 0.75 g (5.25 mmol) of copper (I) oxide and 1.1 g (5 mmol) of methyl i-methyl-2-bromoimidazole- 5-carboxylate were combined in 60 ml of dry dimethylformamide (DMF), and the mixture was heated under reflux overnight. After cooling to room temperature, the reaction mixture was filtered oil with suction through Celite, washed with ethyl acetate and hot methanol, the filtrate was extracted with EDTA solution, the organic phase was separated oil, the solvent was evaporated under reduced pressure and the residue was purified by MPLC on silica gel using the mobile phase cyclohexane/ethyl acetate 1:1. Yield: 247 mg (17.3% of theory). log P[a]: 1.78; log P[n]: 1.80 1H-NMR (CD3CN, 400 MHz); delta 2.23 (s, 6H),3.85 (s, 3H), 3.87 (s, 3H), 6.92 (s, 1H), 7.77 (s, 1H) ppm.

Reference： [1]Patent: US2018/7900,2018,A1 .Location in patent: Paragraph 0406; 0407; 0408; 0409

22
[ 120781-02-4 ]
C₁₁H₁₂N₄O₂S [ No CAS ]

Reference： [1]Patent: US2018/7900,2018,A1

23
[ 120781-02-4 ]
C₁₇H₁₈N₆OS [ No CAS ]

Reference： [1]Patent: US2018/7900,2018,A1

24
[ 120781-02-4 ]
1-methyl-2-bromoimidazole-5-carbonyl bromide [ No CAS ]

Reference： [1]Patent: US2018/7900,2018,A1
[2]Patent: US2019/47982,2019,A1

25
[ 120781-02-4 ]
C₁₁H₁₁BrN₄O [ No CAS ]

Reference： [1]Patent: US2018/7900,2018,A1
[2]Patent: US2019/47982,2019,A1

26
[ 120781-02-4 ]
C₁₅H₁₄N₆OS [ No CAS ]

Reference： [1]Patent: US2018/7900,2018,A1
[2]Patent: US2018/7900,2018,A1

27
[ 120781-02-4 ]
[ 150255-96-2 ]
methyl 2-(3-cyanophenyl)-1-methyl-1H-imidazole-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
239 mg	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In ethanol; toluene; at 80℃;	Methyl 2-bromo-1-methyl-1 H-imidazole-5-carboxylate (659 mg) (3-cyanophenyl) boronic acid (600 mg),(1,1'-diphenylphosphinoferrocene) dichloropalladium (200 mg),2 M aqueous potassium carbonate solution (3 ml),A mixture of toluene (10 ml) and ethanol (3 ml) was stirred at 80 C. overnight.The mixture was cooled to room temperature and extracted with ethyl acetate and water. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane / ethyl acetate) to give the title compound (239 mg)

Reference： [1]Patent: JP2017/222626,2017,A .Location in patent: Paragraph 0230

28
[ 120781-02-4 ]
2-(3-cyanophenyl)-1-methyl-1H-imidazole-5-carboxylic acid [ No CAS ]

Reference： [1]Patent: JP2017/222626,2017,A

29
[ 120781-02-4 ]
3-(5-(((3S)-4-((5-bromopyridin-2-yl)carbonyl)-3-(4-chlorophenyl)piperazin-1-yl)carbonyl)-1-methyl-1H-imidazol-2-yl)benzonitrile [ No CAS ]

Reference： [1]Patent: JP2017/222626,2017,A

30
[ 120781-02-4 ]
methyl 2-(4-(hydroxymethyl)phenyl)-1-methyl-1H-imidazole-5-carboxylate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 4984 - 4995

31
[ 59016-93-2 ]
[ 120781-02-4 ]
C₁₃H₁₄N₂O₃ [ No CAS ]