6-Chloro-biphenyl-3-ylamine synthesis
- Product Name:6-Chloro-biphenyl-3-ylamine
- CAS Number:56970-25-3
- Molecular formula:C12H10ClN
- Molecular Weight:203.67
Yield:56970-25-3 88%
Reaction Conditions:
with tetrakis(triphenylphosphine) palladium(0);sodium carbonate in 1,4-dioxane;water at 110; for 24 h;Inert atmosphere;Suzuki Coupling;
Steps:
4.1.7 4.1.7 6-Chloro-[1,1'-biphenyl]-3-amine (5d)
A mixture of compound 3 (5 mmol), phenylboronic acid (10 mmol), Pd(Ph3P)4 (0.1 mmol), Na2CO3 (10 mmol) in 1,4-dioxane/H2O (20 mL) was stirred at 110 °C for 24 h under Ar.
The reaction mixture was filtered through celite.
The filtrate was concentrated in vacuo and then extracted with EtOAc.
The organic layer was evaporated to give a residue, which was purified by chromatography (petroleum ether/EtOAc, 10:1) to give pure product as a yellow liquid, yield 88%. 1H NMR (400 MHz, Chloroform-d) δ 7.48-7.30 (m, 5H), 7.19 (s, 1H), 6.62 (d, J = 2.7 Hz, 1H), 6.56 (dd, J = 8.5, 2.9 Hz, 1H), 3.65 (s, 2H).
13C NMR (101 MHz, CDCl3) δ 145.24, 141.11, 139.75, 130.55, 129.41 (2CH), 128.06 (2CH), 127.58, 121.57, 117.84, 115.37, 115.36.
References:
Li, Wenlu;Sun, Qinsheng;Song, Lu;Gao, Chunmei;Liu, Feng;Chen, Yuzong;Jiang, Yuyang [European Journal of Medicinal Chemistry,2017,vol. 141,p. 721 - 733]
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