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| | 2,3-Diamino-5-bromopyridine Basic information |
| | 2,3-Diamino-5-bromopyridine Chemical Properties |
| Melting point | 155 °C (dec.) (lit.) | | Boiling point | 180 °C(Press: 0.005-0.01 Torr) | | density | 1.6770 (rough estimate) | | refractive index | 1.6400 (estimate) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | soluble in Methanol | | form | Powder or Needles | | pka | 4.53±0.49(Predicted) | | color | Light yellow to purple or light brown | | Water Solubility | soluble in hot water | | BRN | 119436 | | InChI | InChI=1S/C5H6BrN3/c6-3-1-4(7)5(8)9-2-3/h1-2H,7H2,(H2,8,9) | | InChIKey | YRGMYJUKFJPNPD-UHFFFAOYSA-N | | SMILES | C1(N)=NC=C(Br)C=C1N | | CAS DataBase Reference | 38875-53-5(CAS DataBase Reference) |
| Hazard Codes | Xi,C | | Risk Statements | 36/37/38-34 | | Safety Statements | 26-36-37/39-45-36/37/39 | | WGK Germany | 3 | | Hazard Note | Irritant | | HazardClass | IRRITANT-HARMFUL | | HazardClass | 6.1 | | PackingGroup | III | | HS Code | 29333990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 2,3-Diamino-5-bromopyridine Usage And Synthesis |
| Chemical Properties | light yellow to purple or light brown powder or | | Uses | 2,3-Diamino-5-bromopyridine may be used in the preparation of the following heterocyclic compounds:
- 6-bromoimidazo-[b]pyridine
- 11-bromopyrido[2′,3′:5,6]pyrazino[2,3-f][1,10]phenanthroline
- 6-bromo-3-(tetrahydro-2H-pyran-2-yl)-3H-imidazo[4,5-b]pyridine
| | General Description | 2,3-Diamino-5-bromopyridine can be prepared from 2-amino-3-nitro-5-bromopyridine via reduction using stannous chloride. | | Synthesis | The general procedure for the synthesis of 2,3-diamino-5-bromopyridine from 2-amino-3-nitro-5-bromopyridine is as follows:
Part I: Synthesis of imidazo[4,5-b]pyridin-2(3H)-one boronic acid
Step 1: Preparation of 5-bromopyridine-2,3-diamine
5-Bromo-3-nitropyridin-2-amine (3 g) was dissolved in a solvent mixture of isopropanol (56 mL) and water (28 mL). Ammonium chloride (1.47 g, 2 eq.) and iron powder (2.31 g, 3 eq.) were subsequently added. The reaction mixture was heated to 90°C and kept at this temperature for 45 minutes. Upon completion of the reaction, the mixture was cooled, diluted with ethyl acetate (EtOAc), filtered to remove insoluble matter, and the organic and aqueous layers were separated. The organic layer was subsequently washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the target product 2,3-diamino-5-bromopyridine as a solid (2.45 g, 95% yield).
Product characterization data: 1H-NMR (300 MHz, DMSO-d6) δ 7.25 (d, 1H), 6.77 (d, 1H), 5.70-5.40 (bs, 2H), 5.20-4.80 (bs, 2H). | | References | [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 18, p. 3524 - 3535
[2] Journal of Medicinal Chemistry, 1997, vol. 40, # 22, p. 3679 - 3686
[3] Patent: WO2010/121164, 2010, A2. Location in patent: Page/Page column 60
[4] Patent: EP1460067, 2004, A1. Location in patent: Page 29
[5] Journal of Medicinal Chemistry, 2013, vol. 56, # 3, p. 1160 - 1170 |
| | 2,3-Diamino-5-bromopyridine Preparation Products And Raw materials |
| Raw materials | 2-Amino-5-bromo-3-nitropyridine-->Water-->Isopropyl alcohol-->Carbon-->Iron-->Aluminum chloride | | Preparation Products | 2,3-Pyridinediamine, 5,6-dibromo--->5-Bromo-3-pyrrol-1-yl-pyridin-2-ylamine-->7-Bromo-3-chloro-pyrido[2,3-b]pyrazine-->6-broMo-2,3-diMethyliMidazo[1,2-a]pyridin-8-aMine-->6-Bromo-2-methylimidazo[1,2-a]pyridin-8-ylamine-->6-Bromo-2-ethyl-3H-imidazo[4,5-b]pyridine-->6-BROMO[1,2,5]THIADIAZOLO[3,4-B]PYRIDINE-->7-BroMo-1,2-dihydropyrido[2,3-b]pyrazin-3(4H)-one |
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