705280-65-5|Dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 705280-65-5 ] Purity: 98% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 705280-65-5 ]

CAS No. :	705280-65-5
Formula :	C₇H₇BrN₂O₄
M.W :	263.05
SMILES Code :	COC(=O)C1=C(N=C(Br)N1)C(=O)OC
MDL No. :	MFCD09702026
InChI Key :	JMXUWJPKHDKROF-UHFFFAOYSA-N
Pubchem ID :	21947693

Safety of [ 705280-65-5 ]

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

Application In Synthesis of [ 705280-65-5 ]

* 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 [ 705280-65-5 ]

[ 705280-65-5 ] Synthesis Path-Downstream 1~35

1
[ 705280-65-5 ]
[ 3587-60-8 ]
[ 872182-65-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5397 - 5401.

2
[ 3304-70-9 ]
[ 705280-65-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	With bromine; potassium carbonate; In dichloromethane; acetonitrile; at 20℃; for 12.0h;	a) dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate 9.50 g bromine in 100 ml dichloromethane are added dropwise to a mixture of 9.90 g methyl 1H-imidazole-4,5-dicarboxylate and 7.46 g potassium carbonate in 200 ml dichloromethane and 80 ml acetonitrile. The mixture is stirred for 12 h at ambient temperature in the dark and then added to a saturated aqueous solution of sodium thiosulphate and sodium chloride. The organic phase is separated off and the aqueous phase is extracted several times with ethyl acetate. The combined organic phases are dried over sodium sulphate and the solvent is removed. Yield: 12.31 g (87% of theory) Mass spectrum (ESI+): m/z=263/265 (Br) [M+H]+
87%	With bromine; potassium carbonate; In dichloromethane; acetonitrile; at 20℃; for 2.0h;	At ambient temperature 9.50 g (59.45 mmol) bromine were added dropwise to a solution of 9.90 g (53.76 mmol) dimethyl imidazole-4,5-dicarboxylate in 300 ml dichloromethane and 80 ml acetonitrile. 7.46 g (54.00 mmol) potassium carbonate was added, and the reaction mixture was stirred for 2 hours at ambient temperature. Then the dichloromethane was eliminated using the rotary evaporator and the residue was combined with a saturated solution of sodium chloride and sodium thiosulphate. It was extracted ten times with ethyl acetate, the organic extracts were dried over sodium sulphate and then the solvent was eliminated. Yield: 12.31 g (87% of theory) C7H7BrN2O4 (263.05) Mass spectrum: (M+H)+=263/265 (bromine)
46%	With bromine; potassium carbonate; In dichloromethane; at 20℃; for 1.0h;	EXAMPLE VI Dimethyl 2-bromo-1H-imidazole-4.5-dicarboxylate 6.11 ml bromine are added to 19.80 g dimethyl 1H-imidazole4,5-dicarboxylate and 14.92 g potassium carbonate in 600 ml methylene chloride. The reaction mixture is stirred for one hour at ambient temperature, then a mixture of saturated sodium sulphite solution and saturated sodium chloride solution (1:1) is added. The organic phase is largely separated off and the aqueous phase is extracted with ethyl acetate several times. The combined organic phases are dried over magnesium sulphate and evaporated down, leaving about 7.40 g crude product. The aqueous phase is combined with ethyl acetate and extracted overnight in an extraction apparatus. The ethyl acetate extract is evaporated down and the flask residue is combined with the crude product already obtained. Yield: 13.10 g (46% of theory) Mass spectrum (ESI+): m/z=263, 265 [M+H]+

	With bromine; potassium carbonate; In dichloromethane; acetonitrile; at 20℃; for 2.0h;	To a solution of dibutyl 1H-imidazole-4,5-dicarboxylate (Step 36.1) (20 g, 74.5 mmol) in CH2CI2 (250 mL) and ACN (83 mL) were added successively K2003 (11.33 g, 82 mmol) then dropwise bromine (4.22 mL, 82 mmol). The resulting mixture was stirred 1 hr at RT. The reaction mixture was poured onto aq. Na25203 solution and extracted with CH2CI2. Combined extracts were washed with brine, dried over Mg504, filtered and concentrated under reduced pressure to afford the title product (27.1 g, 74.1 mmol, 99 % yield) as a yellow oil. tR: 1.09 mm (LC-MS 2); ESl-MS: 347/349 [M+H] ESl-MS: 345/347 [M-H] (LC-MS 2); TLC (EtOAc/heptane 1:1) Rf =0.39.The title compound was prepared in analogy to the procedure described in Step 36.2 using methyl 1 H-imidazole-4,5-dicarboxylate at RT for 2 hr. The reaction mixture was quenched with a minimum volume of aq. Na25203 solution and the yellow suspension was filtered and the filtrate was concentrated under reduced pressure. About 30-40 % of the total amount of product was obtained. Most of the product had crystallized and required repeated dissolution with hot THFMeOH 4:1 mixture (500 mL). The extraction from a saturated aq. phase was producing even less product. The individual extracted batches, probably containing some KBr salt, were combined and dried under reduced pressure. The residual salt was always checked after each treatment with THF-MeOH if still some product was present. It required 4 extraction cycles to remove the polar and poorly soluble product from the inorganic salts. TLC (CH2CI2/MeOH 10:1) Rf= 0.42.
8.3 g	With N-Bromosuccinimide; In acetonitrile; at 50℃; for 4.0h;	(1) Dimethyl 1H-imidazole-4,5-dicarboxylate (9.6 g, 52 mmol) was dissolved in acetonitrile (200 mE), and N-bromosuccinimide (13.92 g, 78 mmol) was added thereto, and then the mixture was stirred at 50 C. for 4 hours. After the reaction, water was added and the mixture was extracted twice with ethyl acetate. After being washed with saturated aqueous sodium thiosulfate and saturated aqueous sodium chloride, the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated to obtain dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate (8.3 g). This material was used as is in the next reaction without further purification:10217] ‘H-NMR (CDC13) ö: 10.56 (1H, s), 3.96 (6H, s);10218] ESI-MS mlz=263 (M+H).
	With bromine; In water; at 60℃; for 1.0h;	To a solution of dimethyl 1H-imidazole-4,5-dicarboxylate (1.58g) in water (15mL), was added bromine (4.11g). The mixture was stirred at 60C for Ihr.The solvent was evaporated in vacuo and the residue was triturated with ether to give the target compound (2.35g) as a solid.NMR (DMSO-d6) : d 3.81(6H, s).MASS m/z : 286 (M-l).

References: [1]Tetrahedron Letters,2008,vol. 49,p. 1931 - 1934.
[2]Patent: US2005/203095,2005,A1 .Location in patent: Page/Page column 9.
[3]Patent: WO2005/87774,2005,A1 .Location in patent: Page/Page column 27.
[4]Patent: US2005/261352,2005,A1 .Location in patent: Page/Page column 8.
[5]Patent: WO2005/110999,2005,A1 .Location in patent: Page/Page column 22.
[6]Patent: US2005/26921,2005,A1 .Location in patent: Page/Page column 14.
[7]Patent: WO2004/111051,2004,A1 .Location in patent: Page/Page column 42.
[8]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5397 - 5401.
[9]Patent: WO2014/191894,2014,A1 .Location in patent: Page/Page column 109; 110; 114.
[10]Patent: US2015/284358,2015,A1 .Location in patent: Paragraph 0216; 0217; 0218.
[11]Patent: WO2004/108730,2004,A1 .Location in patent: Page 15.

3
[ 705280-65-5 ]
[ 824-94-2 ]
dimethyl 2-bromo-1-(4-methoxybenzyl)-1H-imidazole-4,5-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 50℃; for 14.0h;	To a solution of dibutyl 2-bromo-1H-imidazole-4,5-dicarboxylate (Step 36.2) (14.2 g, 40.9 mmol) in DMF (100 mL) were added K2C03 (9.61 g, 69.5 mmol) and 1-iodopropane (6.02 mL, 61.3 mmol). The resulting mixture was stirred at 80 C for 1.5 hr. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water and extracted with EtOAc. Combined extracts were washed with brine, dried over Mg504, filtered and concentrated under reduced pressure to afford the title product (14.93 g, 37.6 mmol, 92 % yield) as yellow oil. tR. 1.35 mm (LC-MS 2); ESl-MS: 389/391 [M+H] (LC-MS 2); TLC (hexane/EtOAc 3:1) Rf= 0.38.The title compound was prepared in analogy to the procedure described in Step 36.3 using <strong>[705280-65-5]dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate</strong> (Step 38.1) and 4-methoxybenzyl chloride at 50 00 for 14 hr. The reaction mixture was concentrated under reduced pressure. The residuewas diluted with aq. 10 % Na2003 solution and ice and extracted with EtOAc. Combined extracts were washed with brine, dried over Mg504, filtered and concentrated under reduced pressure to afford a yellow oil. tR: 0.97 mm (LC-MS 2); ESl-MS: 383/385 [M+H] (LC-MS 2); TLC (EtOAc) Rf = 0.75.

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5397 - 5401.
[2]Patent: WO2014/191894,2014,A1 .Location in patent: Page/Page column 110; 114; 115.

4
[ 6974-32-9 ]
[ 705280-65-5 ]
[ 867045-24-7 ]

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 4933 - 4945.

5
[ 705280-65-5 ]
[ 4330-21-6 ]
[ 945229-35-6 ]

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 4933 - 4945.

6
[ 945229-35-6 ]
[ 705280-65-5 ]

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 4933 - 4945.

7
[ 705280-65-5 ]
1-benzyloxymethyl-2-bromo-6-octylamino-1<i>H</i>,7<i>H</i>-1,3,5,7-tetraaza-azulene-4,8-dione [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5397 - 5401.

8
[ 705280-65-5 ]
[ 3355-28-0 ]
[ 705280-60-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 20℃;	EXAMPLE V dimethyl 2-bromo-3-(2-butyn-1-yl)-1H-imidazole-4,5-dicarboxylate 4.53 ml of 1-bromo-2-butyne are added to 13.20 g <strong>[705280-65-5]dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate</strong> and 8.57 g potassium carbonate in 70 ml N,N-dimethylforrnamide and the reaction mixture is stirred overnight at ambient temperature. For working up it is combined with water and extracted with ethyl acetate. The combined organic phases are dried over magnesium sulphate and evaporated down. Yield: 14.58 g (92% of theory) Mass spectrum (ESI+): m/z=315, 317 [M+H]+
75%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 2.0h;Heating / reflux;	136a) dimethyl 2-bromo-1-(but-2-ynyl)-1H-imidazol-4,5-dicarboxylate A solution of 15.0 g (57.0 mmol) of dimethyl 2-bromo-imidazole-4,5-dicarboxylate, 5.15 ml (57.0 mmol) of 1-bromo-2-butyne and 50 ml of N,N-diisopropylethylamine in 280 ml of tetrahydrofuran was refluxed for one hour. The mixture was concentrated by evaporation, the residue combined with approx. 100 ml of water and extracted three times with 70 ml of ethyl acetate. The extracts were washed with 50 ml of water, dried and evaporated down. The crude product thus obtained was purified by column chromatography (silica gel; eluant:dichloromethane with 0-2% ethanol). Yield: 75% of theory. C11H11BrN2O4 (315.13) Rf value: 0.82 (silica gel; dichloromethane/ethanol 9:1) Mass spectrum: (M+H)+=315/317
75%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 1.0h;Heating / reflux;	EXAMPLE I Dimethyl 2-bromo-1-(2-butyn-1-yl)-1H-imidazole-4,5-dicarboxylate A solution of 15.0 g dimethyl 2-bromo-imidazole-4,5-dicarboxylate, 5.15 ml 1-bromo-2-butyne and 50 ml N,N-diisopropylethylamine in 280 ml of tetrahydrofuran is refluxed for one hour. The mixture is concentrated by evaporation, the residue is combined with approx. 100 ml of water and extracted three times with 70 ml of ethyl acetate. The extracts are washed with 50 ml of water, dried and evaporated down. The crude product thus obtained is purified by column chromatography through silica gel with methylene chloride/ethanol (1:0→49:1) as eluant. Yield: 13.50 g (75% of theory) Rf value: 0.82 (silica gel, methylene chloride/ethanol=9:1) Mass spectrum (ESI+): m/z=315/317 (Br) [M+H]+

75%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 1.0h;Heating / reflux;	EXAMPLE IX Dimethyl 2-bromo-1-(2-butyn-1-yl)-1H-imidazole-4,5-dicarboxylate A solution of 15.0 g of dimethyl 2-bromo-imidazole-4,5-dicarboxylate, 5.15 ml of 1-bromo-2-butyne and 50 ml of N,N-diisopropylethylamine in 280 ml of tetrahydrofuran is refluxed for one hour. The mixture is concentrated by evaporation, the residue is combined with approx. 100 ml of water and extracted three times with 70 ml of ethyl acetate. The extracts are washed with 50 ml of water, dried and evaporated down. The crude product thus obtained is purified by column chromatography through silica gel using methylene chloride/ethanol (100:0 to 98:2) as eluant. Yield: 13.50 g (75% of theory) Rf value: 0.82 (silica gel, methylene chloride/ethanol=9:1) Mass spectrum (ESI+): m/z=315, 317 [M+H]+
74%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 12.0h;	b) dimethyl 2-bromo-1-(but-2-ynyl)-1H-imidazole-4,5-dicarboxylate 3.06 g 1-bromo-2-butyne are added dropwise to a mixture of 6.00 g of <strong>[705280-65-5]dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate</strong> and 3.80 g of potassium carbonate in 40 ml of dimethylformamide. The mixture is stirred for 12 h at ambient temperature and then added to an aqueous saturated solution of sodium thiosulphate. The organic phase is separated off and the aqueous phase is extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulphate, the solvent is removed and the residue is chromatographed over silica gel (cyclohexane/ethyl acetate 4:1>1:1). Yield: 5.28 g (74% of theory) Mass spectrum (ESI+): m/z=315/317 (Br) [M+H]+

References: [1]Patent: US2005/26921,2005,A1 .Location in patent: Page/Page column 14.
[2]Patent: WO2004/111051,2004,A1 .Location in patent: Page/Page column 41.
[3]Patent: US2005/20574,2005,A1 .Location in patent: Page/Page column 20-21.
[4]Patent: WO2005/97798,2005,A1 .Location in patent: Page/Page column 22.
[5]Patent: US2005/234235,2005,A1 .Location in patent: Page/Page column 7.
[6]Patent: US2005/143377,2005,A1 .Location in patent: Page/Page column 8.
[7]Patent: WO2005/58901,2005,A1 .Location in patent: Page/Page column 23.
[8]Patent: US2005/203095,2005,A1 .Location in patent: Page/Page column 9.
[9]Patent: WO2005/87774,2005,A1 .Location in patent: Page/Page column 27.

9
[ 705280-65-5 ]
[ 611-17-6 ]
[ 808736-62-1 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 4.0h;	To a solution of <strong>[705280-65-5]dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate</strong> obtained in Preparation 1 (261mg) in dimethylformamide (3mL), was added 2-chlorobenzyl bromide (218mg) and N,N-diisopropylethylamine (0.28mL), and the mixture was stirred at room temperature for 4hrs.The resulting mixture was diluted with ethyl acetate, and washed successively water and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with chloroform and ethyl acetate (4:1) to give the target compound (146mg).NMR (CDC13) : 8 3.81(3H, s), 3.94(3H, s), 5.57(2H, s), 6.52(1H, dd, J=2,8Hz), 7.13 - 7.48(2H, m), 7.42(1H, dd, J=2,8Hz).

References: [1]Patent: WO2004/108730,2004,A1 .Location in patent: Page 15-16.

10
[ 705280-65-5 ]
[ 870-63-3 ]
[ 808736-67-6 ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 50℃; for 2.0h;	A mixture of 12.20 g (46 mmol) dimethyl 2-bromo-imidazole-4,5-dicarboxylate, 7.16 g (48 mmol) 1-bromo-3-methyl-2-butene and 7.19 g (52 mmol) potassium carbonate in 150 ml of dimethylformamide were stirred for two hours at 50 C. Then 100 ml of water were added, and the mixture was extracted three times with ethyl acetate. The extracts were dried and evaporated down. The crude product thus obtained was purified by column chromatography (silica gel; eluant: cyclohexane/ethyl acetate 4:1->2:1). Yield: 13.52 g (89% of theory) C12H15BrN2O4 (331.16) Mass spectrum: (M+H)+=331/333 (bromine)

References: [1]Patent: US2005/261352,2005,A1 .Location in patent: Page/Page column 8.
[2]Patent: WO2005/110999,2005,A1 .Location in patent: Page/Page column 23.

11
[ 705280-65-5 ]
2-butynyl halide [ No CAS ]
[ 705280-60-0 ]

References: [1]Tetrahedron Letters,2008,vol. 49,p. 1931 - 1934.

12
[ 705280-65-5 ]
Me₂CCHCH₂-halide [ No CAS ]
[ 808736-67-6 ]

References: [1]Tetrahedron Letters,2008,vol. 49,p. 1931 - 1934.

13
[ 705280-65-5 ]
o-chlorobenzyl halide [ No CAS ]
[ 808736-62-1 ]

References: [1]Tetrahedron Letters,2008,vol. 49,p. 1931 - 1934.

14
[ 705280-65-5 ]
2-bromo-1-(1,1-dioxo-λ⁶-thietan-3-yl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2015,vol. 51,p. 91 - 94.
Zh. Org. Khim.,2015,vol. 51,p. 94 - 97,4.

15
[ 705280-65-5 ]
dimethyl 2-bromo-1-(1-oxo-λ⁴-thietan-3-yl)-1H-imidazole-4,5-dicarboxylate [ No CAS ]
dimethyl 2-bromo-1-(1-oxo-λ⁴-thietan-3-yl)-1H-imidazole-4,5-dicarboxylate [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2015,vol. 51,p. 91 - 94.
Zh. Org. Khim.,2015,vol. 51,p. 94 - 97,4.

16
[ 705280-65-5 ]
dimethyl 2-bromo-1-(1,1-dioxo-λ⁶-thietan-3-yl)-1H-imidazole-4,5-dicarboxylate [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2015,vol. 51,p. 91 - 94.
Zh. Org. Khim.,2015,vol. 51,p. 94 - 97,4.

17
[ 705280-65-5 ]
2-bromo-1-(thietan-3-yl)-1H-imidazole-4,5-dicarbohydrazide [ No CAS ]
2-bromo-1-(thietan-3-yl)-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2015,vol. 51,p. 91 - 94.
Zh. Org. Khim.,2015,vol. 51,p. 94 - 97,4.

18
[ 705280-65-5 ]
2-bromo-1-(1,1-dioxo-λ⁶-thietan-3-yl)-1H-imidazole-4,5-dicarbohydrazide [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2015,vol. 51,p. 91 - 94.
Zh. Org. Khim.,2015,vol. 51,p. 94 - 97,4.

19
[ 705280-65-5 ]
2-bromo-1-(thietan-3-yl)-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2015,vol. 51,p. 91 - 94.
Zh. Org. Khim.,2015,vol. 51,p. 94 - 97,4.

20
[ 705280-65-5 ]
[ 3221-15-6 ]
dimethyl 2-bromo-1-(thietan-3-yl)-1H-imidazole-4,5-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	With potassium hydroxide; In water; at 55 - 60℃; for 0.5h;	2-Chloromethylthiirane, 0.85 g (7.8 mmol), was added to a solution of 0.44 g (7.8 mmol) of potassium hydroxide and 1.7 g (6.5 mmol) of ester 1 in 30 mL of water, and the mixture was stirred for 30 min at 55-60C. The mixture was cooled, and the precipitate was filtered off and washed with a solution of KOH and water. Yield 0.36 g (16%), mp 156-158C (from EtOH), Rf 0.70. IR spectrum, ν, cm-1: 1729 (C=O), 1560 (C=N). 1H NMR spectrum (CDCl3), δ, ppm: 3.31-3.40 m (2H,(CH2SCH2), 3.86 s and 3.99 s (3H each, OCH3), 4.12-4.21 m (2H, CH2SCH2), 5.88-6.02 m (1H, NCH).13C NMR spectrum (CDCl3), δC, ppm: 33.70 (SCH2), 52.35 and 52.75 (OCH3), 53.40 (NCH), 122.14 (C2),128.58 (C4, C5), 160.41 and 161.35 (C=O). Found, %:C 35.91; H 3.24; N 8.41. C10H11BrN2O4S. Calculated,%: C 35.82; H 3.28; N 8.36.

References: [1]Russian Journal of Organic Chemistry,2015,vol. 51,p. 91 - 94.
Zh. Org. Khim.,2015,vol. 51,p. 94 - 97,4.

21
[ 705280-65-5 ]
[ 925-90-6 ]
methyl 2-bromo-4-(2-hydroxypropan-2-yl)-1H-imidazole-5-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
830 mg	In tetrahydrofuran; at -10℃; for 0.666667h;Inert atmosphere;	(2) Under a nitrogen atmosphere, dimethyl 2-bromo- 1H-imi- dazole-4,5-carboxylate (2 g, 7.6 mmol) was dissolved in THF (38 mE) and, at -40 C., a 1 M solution (30 mE) of EtMgl3r in THF was added dropwise thereto over a period of 10 minutes. Afier allowing the mixture to react for further 30 minutes, the reaction was quenched by the addition of aqueous ammonium chloride. Water was added and the mixture was extracted twice with ethyl acetate. After being washed with saturated aqueous sodium chloride, the organic layer was dried over anhydrous sodium sulfate. Afier concentrating the organic layer, the residue was purified by colunm chromatography to obtain methyl 2-bromo-4-(2-hydroxypropan- 2-yl)-1H-imidazole-5-dicarboxylate (830 mg):10219] ‘H-NMR(CDC13) ö: 9.78 (1H, s), 3.93 (3H, s), 1.68 (3H, s), 1.61 (3H, s);10220] ESI-MS mlz=263 (M+H).

References: [1]Patent: US2015/284358,2015,A1 .Location in patent: Paragraph 0216; 0218; 0219; 0220.

22
[ 705280-65-5 ]
methyl 2-bromo-1-(2,5-dichlorobenzyl)-4-(2-hydroxypropan-2-yl)-1H-imidazole-5-carboxylate [ No CAS ]