N,N'-Dimethylethylenediamine → 4-Iodo-1H-benzimidazole

Two reactions were set up as follows: A mixture of 4-bromo-1H-benzimidazole (725 mg, 3.68 mmol), sodium iodide dihydrate (1.37 g, 7.36 mmol), copper(I) iodide (70 mg, 0.37 mmol) and N,N′-dimethylethylenediamine (78 μL, 65 mg, 0.74 mmol) in dioxane (8 mL) was irradiated at 150° C. in a microwave reactor for 2.5 hours. The two reaction mixtures were combined, diluted with water (90 mL) and conc. ammonia (20 mL), then extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with water (20 mL), then with saturated sodium chloride solution (50 mL), dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel, eluting with ethyl acetate, yielding the product as a yellow-white solid (1.40 g, 78%). 1H NMR (400 MHz, d6-DMSO): δ 12.72 (1H, s), 8.28 (1H, s), 7.61-7.53 (2H, m), 7.01 (1H, t, J=7.8 Hz); m/z (ES+) 245 [MH+].

1. customwas irradiated at 150° C. in a microwave reactor for 2.5 hours
2. customThe two reaction mixtures
3. extractionextracted with ethyl acetate (3×50 mL)
4. washThe combined organic layers were washed with water (20 mL)
5. dry with materialwith saturated sodium chloride solution (50 mL), dried (MgSO4)
6. concentrationconcentrated in vacuo
7. customThe crude product was purified by flash chromatography on silica gel
8. washeluting with ethyl acetate

ORD record

ord-4419d7907f4c40be8385cea827892086

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07592456B2