3-BroMo-6-(furan-2-yl)pyrazine-2-carbonitrile synthesis
- Product Name:3-BroMo-6-(furan-2-yl)pyrazine-2-carbonitrile
- CAS Number:1351238-40-8
- Molecular formula:C9H4BrN3O
- Molecular Weight:250.05
120930-05-4
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1351238-40-8
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Yield:1351238-40-8 39.7%
Reaction Conditions:
with tert.-butylnitrite;copper(ll) bromide in N,N-dimethyl-formamide at 55; for 0.833333 h;Sandmeyer Reaction;
Steps:
50.4
Step 4: synthesis of 3-bromo-6-(furan-2-yl)pyrazine-2-carbonitrile (57)To a solution of copper(ii) bromide (2.88 g, 12.89 mmol) in DMF (10 mL) at 55°C was added tert-butylnitrite (3.09 mL, 2.66 g, 25.8 mmol). A solution of 3-amino-6-(furan-2- yl)pyrazine-2-carbonitrile 56 (2.4 g, 12.89 mmol) in DMF (10 mL) was added drop wise (in 30 min). After addition was complete, the reaction was stirred for 20 min. Quenched with 60 mL 3N HC1 contain 4 mL concentrated H2S04 at -20°C. The resulting precipitate was collected. Purification by chromatography (toluene) gave 3- bromo-6-(furan-2-yl)pyrazine-2-carbonitrile 57 (1.28 g, 39.7 %). NMR (400 MHz, CDCls) 6.63 (q, J= 3.5 and 1.5 Hz, 1H), 7.30 (dd, J= 3.5 and 0.8 Hz, 1H), 7.66 (dd, J= 2.0 and 0.8 Hz, 1H), 8.86 (s, 1H). (m/z) = 250 and 252 (M+H)+.
References:
WO2011/147764,2011,A1 Location in patent:Page/Page column 69
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