120935-94-6|Methyl 4-bromo-2,5-dimethyl-1H-pyrrole-3-carboxylate| Ambeed

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Quality Control of [ 120935-94-6 ] Purity: 98% SDS Specification

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Product Details of [ 120935-94-6 ]

CAS No. :	120935-94-6
Formula :	C₈H₁₀BrNO₂
M.W :	232.07
SMILES Code :	O=C(C1=C(C)NC(C)=C1Br)OC
MDL No. :	MFCD00203873
InChI Key :	LGBDYFSMZPRVLL-UHFFFAOYSA-N
Pubchem ID :	2798469

Safety of [ 120935-94-6 ]

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

Application In Synthesis of [ 120935-94-6 ]

* 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 [ 120935-94-6 ]

[ 120935-94-6 ] Synthesis Path-Downstream 1~23

1
[ 69687-80-5 ]
[ 120935-94-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With pyridinium hydrobromide perbromide; triethylamine; In dichloromethane; at 0℃; for 2h;	To a mixture of methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate 21 (6.85 g, 45.0 mmol), triethylamine (8.7 mL, 63.0 mmol) and CH2Cl2 (270 mL) was added pyridinium bromide perbromide (15.7 g, 15.7 mmol) portionwise at 0 C. After stirring at 0 C for 2 h, the mixture was poured into brine and extracted with EtOAc. The organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc). The product was recrystallized from hexane-EtOAc to give 22 (7.59 g, 92%) as yellow crystals. 1H NMR (300 MHz, CDCl3) delta: 2.19 (3H, s), 2.47 (3H, s), 3.82 (3H, s), 8.20 (1H, s).
	With pyridine perbromohydrobromide; triethylamine; In dichloromethane; at 0℃; for 2h;	4-bromo-2,5-dimethyl-1H-pyrrole-3-carboxylate To a solution of methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate (6.85 g) and triethylamine (8.7 ml) in dichloromethane (270 ml) was added pyridine perbromohydrobromide (15.7 g) little by little at 0 C. The reaction mixture was stirred at the same temperature for 2 hours and poured into saturated sodium chloride solution.. The reaction mixture was extracted with ethyl acetate, and the ethyl acetate layer was dried over magnesium sulfate and concentrated.. The residue was purified by column chromatography (carrier: silicagel, eluant: hexane-ethyl acetate) and recrystallized from ethyl acetate-hexane to obtain the titled compound (7.59 g) as yellow crystals.1H-NMR (CDCl3) delta 2.19 (3H, s), 2.47 (3H, s), 3.82 (3H, s), 8.20 (1H, s).

References: [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 422 - 434.
[2]Journal of Medicinal Chemistry,1993,vol. 36,p. 2739 - 2744.
[3]Patent: EP1466902,2004,A1 .Location in patent: Page 31.

2
[ 76513-69-4 ]
[ 120935-94-6 ]
[ 120935-95-7 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	b) Methyl 4-Bromo-2,5-dimethyl-1-((2-(trimethylsilyl) ethoxy)methyl)-1H-pyrrole-3-carboxylate The product of step a) (2g, 8.62mmol) in tetrahydrofuran (20ml) was added dropwise to a stirred and ice-cooled suspension of sodium hydride (0.3g, 12.5mmol) in tetrahydrofuran (60ml). After stirring at room temperature for 45 minutes the resulting pale yellow suspension was treated with (2-(trimethylsilyl) ethoxy)methyl chloride (1.7ml, 10.2mmol). After stirring for 2 hours at room temperature the reaction was quenched with water (5ml) and evaporated to near dryness. The residue was extracted with chloroform and the combined extracts dried (MgSO4) and evaporated. Chromatography of the resulting oil on silica eluding with ethyl acetate-hexane mixtures gave the sub-title compound (2.67g), M+361/363.

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 2739 - 2744.
[2]Patent: EP300688,1989,A1 .

3
[ 120935-94-6 ]
[ 120934-96-5 ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 2739 - 2744.

4
[ 120935-94-6 ]
[ 120935-96-8 ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 2739 - 2744.

5
[ 1765-93-1 ]
[ 120935-94-6 ]
methyl 4-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In DMF (N,N-dimethyl-formamide); water; at 130℃; for 20h;	Example 14 Production of methyl 4-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate To a mixture of the compound (0.23 g) produced in Reference Example 2, 4-fluorophenylboronic acid (0.15 g), tetrakis(triphenylphosphine)palladium (0.06 g) and anhydrous sodium carbonate (0.32 g) were added dimethylformamide (8 ml) and water (2 ml) and the mixture was heated at 130 C for 20 hours and cooled to room temperature.. To the resulting reaction mixture was added water and extracted with ethyl acetate.. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated.. The resulting crude product was purified by column chromatography (carrier: silicagel, eluant: hexane-ethyl acetate) to obtain the titled compound (138 mg) as pale yellow crystals.1H-NMR (CDCl3) delta 2.09 (3H, s), 2.51 (3H, s), 3.62 (3H, s), 6.9-7.1 (2H, m), 7.1-7.3 (2H, m), 7.99 (1H, s). IR (KBr): nu 3287, 3096, 2994, 2949, 1667 cm-1.

References: [1]Patent: EP1466902,2004,A1 .Location in patent: Page 40.

6
[ 69687-80-5 ]
[ 39416-48-3 ]
[ 120935-94-6 ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform;	a) Methyl 4-Bromo-2,5-dimethyl-1H-pyrrole-3-carboxylate A stirred solution of methyl 2,5-dimethyl-1H-pyrrole -3-carboxylate (1.5g, 9.8mmol) in chloroform (60ml) and triethylamine (2.5ml) cooled to 0C was treated portionwise with pyridinium perbromide (3.5g, 10.94 mmol). The mixture was allowed to warm to room temperature and then silica (6g) was added in one portion and the entire mixture evaporated to dryness under reduced pressure (14 mm Hg) with gentle heating (below 50). Chromatography on silica eluding with ethyl acetate-hexane mixtures gave the sub-title compound (1.9g), M+231/233.

References: [1]Patent: EP300688,1989,A1 .

7
[ 100-39-0 ]
[ 120935-94-6 ]
methyl 1-benzyl-4-bromo-2,5-dimethyl-1H-pyrrole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%		General procedure: To a suspension of NaH (60% in mineral oil, 0.03 g, 0.80 mmol) in THF (1 mL) was added a solution of 1 (0.23 g, 0.80 mmol) in THF (1 mL) dropwise at 0 C. After stirring at 0 C for 1 h, methyl iodide (0.05 mL, 0.80 mmol) was added. The mixture was stirred at 0 C for 3 h, poured into brine, and extracted with EtOAc. The organic layer was dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc). The product was recrystallized from hexane-EtOAc to give 2 (0.09 g, 69%) as yellow crystals.
		Reference Example 4 Production of methyl 1-benzyl-4-bromo-2,5-dimethyl-1H-pyrrole-3-carboxylate A suspension of sodium hydride (60% suspension of sodium hydride in oil, 0.26 g) in tetrahydrofuran (30 ml) was cooled on a ice bath, and to the suspension was added the compound (1.01 g) produced in Reference Example 2.. The reaction mixture was heated at the same temperature for 30 minutes.. To the reaction mixture was added benzyl bromide (0.57 ml), and the reaction mixture was stirred at room temperature for 4 hours.. The reaction mixture was poured into saturated aqueous solution of sodium chloride and the reaction mixture was extracted with ethyl acetate.. The ethyl acetate layer was dried over magnesium sulfate and concentrated.. The residue was purified by column chromatography (carrier: silicagel, eluant: hexane-ethyl acetate), and recrystallized from ethyl acetate-hexane to obtain the titled compound (0.75 g) as colorless crystals.1H-NMR (CDCl3) delta 2.15 (3H, s), 2.45 (3H, s), 3.84 (3H, s), 5.08 (2H, s), 6.8-7.0 (2H, m), 7.2-7.4 (3H, m).

References: [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 422 - 434.
[2]Patent: EP1466902,2004,A1 .Location in patent: Page 32.

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[ 120935-94-6 ]
[ 1320232-56-1 ]