1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Methyl 2,4-dibromothiazole-5-carboxylate

A solution of 2,4-dibromo-thiazole-5-carboxylic acid (1.7 g, 5.92 mmol) in methanol (20 ml) was treated with N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (920 mg, 5.92 mmol). The mixture was stirred at ambient temperature overnight. The solvent was evaporated and water (30 ml) was added. The mixture was then extracted with 3×30 ml of EtOAc. The combined organics were washed with brine, dried with MgSO4 and concentrated in vacuo. The crude was purified by flash chromatography (0 to 5% EtOAc/Hexanes) to afford 2,4-Dibromo-thiazole-5-carboxylic acid methyl ester (1.4 g, 78%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 3.91 (s, 3H).

1. customThe solvent was evaporated
2. additionwater (30 ml) was added
3. extractionThe mixture was then extracted with 3×30 ml of EtOAc
4. washThe combined organics were washed with brine
5. dry with materialdried with MgSO4
6. concentrationconcentrated in vacuo
7. customThe crude was purified by flash chromatography (0 to 5% EtOAc/Hexanes)

ORD record

ord-6af32ca2635141ed8b014e6444daca2b

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07504513B2