| Identification | More | [Name]
Methyl 4-bromopyrrole-2-carboxylate | [CAS]
934-05-4 | [Synonyms]
METHYL 4-BROMO-1H-PYRROLE-2-CARBOXYLATE
METHYL 4-BROMOPYRROLE-2-CARBOXYLATE
RARECHEM AL BF 1264 | [Molecular Formula]
C6H6BrNO2 | [MDL Number]
MFCD00832855 | [Molecular Weight]
204.02 | [MOL File]
934-05-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
100-101°C | [Boiling point ]
290.5±20.0 °C(Predicted) | [density ]
1.674±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder to crystal | [pka]
13.49±0.50(Predicted) | [color ]
White to Orange to Green | [λmax]
271nm(MeOH)(lit.) | [InChI]
InChI=1S/C6H6BrNO2/c1-10-6(9)5-2-4(7)3-8-5/h2-3,8H,1H3 | [InChIKey]
ZXFCRVGOHJHZNF-UHFFFAOYSA-N | [SMILES]
N1C=C(Br)C=C1C(OC)=O | [CAS DataBase Reference]
934-05-4(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white powder | [Uses]
4-Bromo-1H-pyrrole-2-carboxylic Acid Methyl Ester is a useful synthetic intermediate. It is used to synthesize potent melanin-concentrating hormone (MCH-R1) antagonists based on pyrazolopiperazinone. | [Synthesis]
Example 1C. Synthesis of 4-bromo-2-methoxycarbonylpyrrole: To a solution of methanol (100 mL) containing 1-(4-bromo-1H-pyrrol-2-yl)-2,2,2-trichloroacetophenone (20 g, 68 mmol) was added slowly and dropwise sodium methanol (1M solution in methanol, 34 mL, 34 mmol). The reaction mixture was stirred at room temperature for 1 hour and then diluted with water (300 mL) to separate the organic layer. The aqueous phase was extracted with dichloromethane (CH2Cl2), and the combined organic layer and extract were washed with water (2 x 50 mL), dried over anhydrous magnesium sulfate (MgSO4), and concentrated under reduced pressure. The residue was recrystallized by hexane to give 4-bromo-2-methoxycarbonylpyrrole (12 g, 85% yield) as a white solid.LC-MS analysis showed [M-H]+ peak at 203.1.1.1H NMR (DMSO-d6, 400 MHz) data were as follows: δ 12.31 (broad single peak, 1H), 7.16 (single peak, 1H), 6.81 (single peak, 1H ), 3.75 (single peak, 3H). | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 20, p. 4412 - 4418
[2] Patent: WO2010/42682, 2010, A1. Location in patent: Page/Page column 50
[3] Patent: US2006/293320, 2006, A1. Location in patent: Page/Page column 25; 35 |
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