5-(1H-imidazol-2-yl)-2-methylaniline synthesis
- Product Name:5-(1H-imidazol-2-yl)-2-methylaniline
- CAS Number:1126367-12-1
- Molecular formula:C10H11N3
- Molecular Weight:173.21
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Yield:1126367-12-1 42.9%
Reaction Conditions:
with potassium acetate;tetrakis(triphenylphosphine) palladium(0) in 1,4-dioxane;water at 150; for 0.5 h;Product distribution / selectivity;microwave irradiation;
Steps:
117.117a
A mixture of 2-iodo-lH-imidazole (4.7 g, 24.23 mmol), 3-amino-4- methylphenylboronic acid hydrochloride (4.6 g, 24.54 mmol), KOAc (7.13 g, 72.69 mmol) and Pd(PPh3^ (1.400 g, 1.21 mmol) in dioxane (30 mL) and water (7.50 mL) was subjected to microwave for 0.5h at 150 0C. The mixture was concentrated in vacuo and the residue was purified with ISCO MPLC (0-6% MeOH /DCM) to yield a brown solid that was repurified with Gilson HPLC (1-40% MeCN/0.1%TFA in water) to yield the title compound as a solid (1.800 g, 42.9 %). 1U NMR (DMSO-d6) 67.85 (s, 2 H), 7.14 - 7.35 (m, 3 H), 2.26 (s, 3 H). MS (M+H+) = 174.
References:
WO2009/27746,2009,A1 Location in patent:Page/Page column 105
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1126369-31-0
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