ChemicalBook CAS DataBase List 5-Fluoro-3-methylindole

5-Fluoro-3-methylindole synthesis

5synthesis methods

Product Name:5-Fluoro-3-methylindole
CAS Number:392-13-2
Molecular formula:C9H8FN
Molecular Weight:149.16

2338-71-8 Synthesis

2338-71-8
166 suppliers
$15.00/250mg

392-13-2
127 suppliers
$32.00/100mg

Yield: 82.3%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 70; for 2 h;

Steps:

58.1 Step 1) Synthesis of 5-fluoro-3-methyl-1H-indole
5-Fluoro-1H-indole-3-carbaldehyde (3.2 g, 19.6 mmol) was dissolved in 10 mL of anhydrous tetrahydrofuran, then lithium aluminium hydride (2.61 g, 68.6 mmol) was added to the solution. The mixture was reacted at 70 °C for 2 hours. After the reaction, the reaction mixture was cooled to RT and quenched with aqueous sodium hydroxide (18 mL, 2 0%). 60 mL of dichloromethane was added to the mixture and the resulting mixture was washed with saturated aqueous sodium chloride (40 mL). The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography eluted with PE/EA(V/V)=50/1 to give the title compound as a light yellow solid (2.41 g, 82.3%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z:150.2 [M+Hfb; and ‘H NMR (400 MHz, CDC13): 6 7.30-7.23 (m, 2H), 7.04 (s, 1H), 6.97 (td, J = 9.0, 2.0 Hz, 1H), 2.33 (s, 3H).

References:

SUNSHINE LAKE PHARMA CO., LTD.;ZHANG, Yingjun;JIN, Chuanfei;ZHONG, Wenhe;ZHANG, Ji;GAO, Li;CHEN, Kangzhi WO2015/90233, 2015, A1 Location in patent:Paragraph 00362

67-56-1 Synthesis