| Identification | Back Directory | [Name]
3-amino-5-bromopyridine-2-carboxylic acid | [CAS]
870997-85-6 | [Synonyms]
3-Amino-5-bromopyridine-2...
3-Amino-5-bromopicolinic acid
3-AMino-5-broMopyridine-2-carboxylic
3-AMino-5-broMopyridin-2-carboxylic acid
3-amino-5-bromopyridine-2-carboxylic acid
3-amino-5-bromo-2-Pyridinecarboxylic acid
2-Pyridinecarboxylic acid, 3-aMino-5-broMo- | [Molecular Formula]
C6H5BrN2O2 | [MDL Number]
MFCD09999770 | [MOL File]
870997-85-6.mol | [Molecular Weight]
217.02 |
| Chemical Properties | Back Directory | [Melting point ]
>170°C (dec.) | [Boiling point ]
399.0±42.0 °C(Predicted) | [density ]
1.909±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
4.15±0.10(Predicted) | [color ]
Yellow | [InChI]
InChI=1S/C6H5BrN2O2/c7-3-1-4(8)5(6(10)11)9-2-3/h1-2H,8H2,(H,10,11) | [InChIKey]
GXXIHPZAIYKHGG-UHFFFAOYSA-N | [SMILES]
C1(C(O)=O)=NC=C(Br)C=C1N |
| Hazard Information | Back Directory | [Uses]
3-amino-5-bromopyridine-2-carboxylic acid is used in the preparation of biological reagents such as macrocyclic glucagon-like peptide 1 receptor agonists. It is also used in the preparation of pyridinamide and indoline compounds. | [Synthesis]
Step 2: Synthesis of 3-amino-5-bromopyridine-2-carboxylic acid
To a 100 mL round bottom flask was added 3-amino-5-bromopyridine-2-carboxamide (1.05 g, 4.9 mmol) and aqueous sodium hydroxide solution (0.98 g dissolved in 10 mL of water, 24.5 mmol). The reaction mixture was heated to reflux temperature and stirred for 5 hours. Upon completion of the reaction, volatiles were removed by distillation under reduced pressure to give a residue. The residue was neutralized with 2N HCl at 0 °C to pH=7.0 and precipitate was precipitated. The precipitate was collected by filtration and dried to give 3-amino-5-bromopyridine-2-carboxylic acid as a light yellow solid (1 g, 95% yield).
1H NMR (300 MHz, DMSO-d6): δ 7.65 (d, J=2.1 Hz, 1H), 7.20 (d, J=2.1 Hz, 1H), 7.01-7.16 (br s, 2H).
LC-MS (ESI): calculated: 215.9; measured: 217.0 [M+H]+ (RT: 0.43 min). | [References]
[1] Patent: WO2012/58671, 2012, A1. Location in patent: Page/Page column 117-118
[2] Patent: US2014/38952, 2014, A1. Location in patent: Page/Page column 0180-0181
[3] Patent: EP1757594, 2007, A1. Location in patent: Page/Page column 77
[4] Patent: WO2008/76425, 2008, A1. Location in patent: Page/Page column 33
[5] Patent: WO2008/130600, 2008, A2. Location in patent: Page/Page column 56 |
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