6-THIEN-2-YLPYRID-3-YLAMINE synthesis
- Product Name:6-THIEN-2-YLPYRID-3-YLAMINE
- CAS Number:898289-44-6
- Molecular formula:C9H8N2S
- Molecular Weight:176.24
13534-97-9
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Yield:898289-44-6 92.8%
Reaction Conditions:
with dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2;sodium hydrogencarbonate in 1,4-dioxane at 100; for 1 h;Inert atmosphere;
Steps:
10
[00222] A flask charged with 6-bromopyridin-3 -amine (346 mg, 2.0 mmol), (thiophen-2- yl)boronic acid (307 mg, 2.4 mmol), Pd(dppf)Ci2.CH2Ci2 (173 mg, 0.2 mmol) and saturated aHC03 solution (2 mL) was purged with nitrogen followed by the addition of 1,4-dioxane (6 mL). The mixture was stirred and heated to 100 °C for an hour, then cooled to room temperature, and filtered. The filtrate was extracted with ethyl acetate, and washed with saturated brine. The combined organic phases were dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel column (PE/EA = 1/1) to give 6- (thiophen-2-yl)pyridin-3 -amine (327 mg, 92.8%) as a yellow solid. XH NMR (400 MHz, CDC13) δ 8.07 (d, J= 2.0 Hz, 1H), 7.47 (d, J= 8.4 Hz, 1H), 7.39 (dd, J= 1.2 Hz, 4.0 Hz, 1H), 7.27 (dd, J= 1.2 Hz, 5.2 Hz, 1H), 7.07-7.05 (m, 1H), 6.99 (dd, J= 2.8 Hz, 8.8 Hz, 1H). ES-MS m/z: 177 [M+H]+. LC-MS Purity (214 nm): >97%; tR = 1.53 min.
References:
WO2016/73891,2016,A1 Location in patent:Paragraph 00222
131941-31-6
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4487-59-6
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