ChemicalBook CAS DataBase List 3-(2-THIENYL)ANILINE

3-(2-THIENYL)ANILINE synthesis

8synthesis methods

Product Name:3-(2-THIENYL)ANILINE
CAS Number:92057-12-0
Molecular formula:C10H9NS
Molecular Weight:175.25

6165-68-0 Synthesis

6165-68-0
401 suppliers
$14.00/5g

591-19-5
334 suppliers
$10.00/10g

92057-12-0
48 suppliers
$76.00/250mg

Yield:92057-12-0 83%

Reaction Conditions:

with tetrakis(triphenylphosphine) palladium⁽⁰⁾;potassium carbonate in tetrahydrofuran;water at 80; for 12 h;Suzuki Coupling;

Steps:

4.6.2 Synthesis of fragment screening hits 1-4 4.6.2.1 3-(thiophen-2-yl)aniline (1)

Compound 1 was synthesized according to reported conditions.⁶⁰ Briefly, 3-bromoaniline (0.172g, 1.0mmol, 1.0eq) was dissolved in 10mL THF to give a clear solution. Potassium carbonate (0.415g, 3.0mmol, 3.0eq) dissolved in 2mL H₂O was added, followed by 2-thienylboronic acid (0.166g, 1.3mmol, 1.3eq). Tetrakis(triphenylphosphine)palladium(0) (0.034g, 0.03mmol, 0.03eq) was then added, and the reaction solution was heated to reflux at 80°C for 12h until TLC in 50:50 hexanes:EtOAc indicated completion (Rf=0.5); staining with ρ-anisaldehyde gave a purple spot for product. EtOAc (100mL) was added to the reaction and it was extracted with H₂O (3×35mL), then brine (1×35mL), dried with Na₂SO₄, filtered, and evaporated under rotary vacuum to give a reddish brown oil. The crude product was purified by silica gel chromatography in 75:25 hexanes:EtOAc; pure fractions were combined and evaporated under reduced pressure to yield 1 as a bright yellow crystalline solid (144mg, 83%): MS m/z 176.1 (M+H); ¹H NMR (400MHz, d₆-DMSO): δ 7.67,7.61 (m, 5H), 7.28 (d, 1H), 7.17 (t, J=4Hz, 1H).

References:

Makley, Leah N.;Johnson, Oleta T.;Ghanakota, Phani;Rauch, Jennifer N.;Osborn, Delaney;Wu, Taia S.;Cierpicki, Tomasz;Carlson, Heather A.;Gestwicki, Jason E. [Bioorganic and Medicinal Chemistry,2021,vol. 34]