2-CHLORO-6-PHENYLPYRAZINE synthesis
- Product Name:2-CHLORO-6-PHENYLPYRAZINE
- CAS Number:41270-62-6
- Molecular formula:C10H7ClN2
- Molecular Weight:190.63
4774-14-5
98-80-6
41270-62-6
General procedure for the synthesis of 2-chloro-6-phenylpyrazine: to a solvent mixture of 2,6-dichloropyrazine (2.0 eq.) dissolved in a 3:1 ratio of aqueous DME with 2M sodium carbonate (0.125 M), phenylboronic acid (1.0 eq.) was added, followed by the addition of PdCl2(dppf)-DCM adduct (0.1 eq.). The reaction mixture was placed in a microwave reactor and heated at 120 °C for 15 min. After completion of the reaction, the crude product was diluted with ethyl acetate and washed with saturated aqueous NaHCO3 solution. After the aqueous phase was saturated with sodium chloride, the organic phase was dried with magnesium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography with the eluent being heptane to a heptane solution containing 30% ethyl acetate, resulting in 2-chloro-6-phenylpyrazine in 75% yield.LC/MS analysis showed a m/z of 191.0 (MH+) and a retention time (Rt) of 1.00 min.
Yield:41270-62-6 75%
Reaction Conditions:
with sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 in 1,2-dimethoxyethane;water at 120; for 0.25 h;Microwave irradiation;Suzuki Coupling;
Steps:
Synthesis o -chloro-6-phenylpyrazine[00145] To a solution of 2,6-dichloropyrazine (2.0 equiv.) in 3 : 1 DME:2M aqueous sodium carbonate (0.125 M) was added phenylboronic acid (1.0 equiv.) then PdCl2(dppf) · DCM adduct (0.1 equiv.). The reaction was heated in the microwave at 120 °C for 15 minutes. The crude reaction mixture was diluted with ethyl acetate and washed with sat. aq. sodium bicarbonate then sat. NaCl. The organic phase was dried with magnesium sulfate, filtered, and concentrated. The crude material was purified by silica gel column chromatography with heptanes to 30% ethyl acetate in heptanes to give 2- chloro-6-phenylpyrazine in 75% yield. LC/MS (m/z): 191.0 (MH+), R, = 1.00 min.
References:
WO2012/4217,2012,A1 Location in patent:Page/Page column 63
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