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ChemicalBook CAS DataBase List 4-phenylindoline
179473-53-1

4-phenylindoline synthesis

5synthesis methods
4-phenylindoline

179473-53-1
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Yield:179473-53-1 100%

Reaction Conditions:

with sodium cyanoborohydride;acetic acid at 20; for 1 h;

Steps:

10.b Step b.

To a stirred solution of 4-phenyl-lH-indole (0.25 g, 1.29 mmol) in acetic acid (3 ml) was added NaCNBH3 (0.089 g, 1.42 mmol) at rt. The reaction mixture was stirred at rt for 1 h. The resulting mixture was basified with saturated NaHCC>3 solution and extracted with EtOAc (3 x 20 ml). The combined organic phase was washed with brine (20 ml), dried over Na2S04, filtered and concentrated under reduced pressure yielding 4 -phenylindoline (0.37 g, quantitative). This material was used for the next step without further purification. LCMS: Method C, 1.78 min, MS: ES+ 195.8; NMR (400 MHz, DMSO-d6) δ ppm 7.44 - 7.51 (m, 4 H), 7.31 - 7.35 (m, 1 H), 7.01 (t, J=7.6 Hz, 1 H), 6.59 (d, J=7.2 Hz, 1 H), 6.51 (d, J=7.6 Hz, 1 H), 5.60 (s, 1 H), 3.39 (t, J=8.4 Hz, 2 H), 2.98 (t, J=8.4 Hz, 2 H).

References:

WO2017/141036,2017,A1 Location in patent:Page/Page column 46; 55; 56