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ChemicalBook CAS DataBase List 3-bromothieno[3,2-c]pyridin-4-amine

3-bromothieno[3,2-c]pyridin-4-amine synthesis

6synthesis methods
-

Yield:799293-85-9 94%

Reaction Conditions:

with ammonia in 1,4-dioxane;water at 150; for 18 h;

Steps:

219.A EXAMPLE 219; 3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-4-amine; EXAMPLE 219A; 3-bromothieno[3,2-c]pyridin-4-amine
A mixture of 3-bromo-4-chlorothieno[3,2-c]pyridine (prepared according to the procedure described in Bull. Soc. Chim. Belges 1970, 79, 407-414, 3 g, 12 mmol), concentrated aqueous NH4OH (100 mL), and p-dioxane (100 mL) was sealed in a stainless steel, high-pressure reactor and stirred for 18 hours at 150 C. The mixture was concentrated to half its original volume, diluted with water, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), filtered, and concentrated to provide 2.6 g (94%) of the desired product. 1H NMR (DMSO-d6, 400 MHz) ? 7.83 (d, 1H), 7.77 (s, 1H), 7.26 (d, 1H), 6.48 (br s, 2H); MS m/e 229 (M+H)+.

References:

Betschmann, Patrick;Burchat, Andrew;Calderwood, David;Curtin, Michael L.;Davidsen, Steven K.;Davis, Heather M.;Frey, Robin R.;Heyman, Howard R.;Hirst, Gavin;Hrnciar, Peter;Michaelides, Michael;Rafferty, Paul US2005/20619, 2005, A1 Location in patent:Page 47

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