ChemicalBook CAS DataBase List Indole-3-acetone

Indole-3-acetone synthesis

10synthesis methods

Product Name:Indole-3-acetone
CAS Number:1201-26-9
Molecular formula:C11H11NO
Molecular Weight:173.21

75-16-1

2-(1H-indol-3-yl)-N-Methoxy-N-MethylacetaMide

132922-37-3

1201-26-9

a) Under argon protection, 2-(1H-indol-3-yl)-N-methoxy-N-methylacetamide (3.00 g, 13.75 mmol) was dissolved in anhydrous THF (60 mL) and the solution was cooled to 0 °C. A THF solution of methylmagnesium bromide (27.49 mL, 27.49 mmol) was added slowly and dropwise with continuous stirring. After 2 hours of reaction, the same amount of methylmagnesium bromide solution (27.49 mL, 27.49 mmol) was added again, and a third addition of methylmagnesium bromide solution (27.49 mL, 27.49 mmol) was made after 3 hours. Upon completion of the reaction, the reaction was quenched by the addition of saturated aqueous ammonium chloride solution, followed by the addition of ethyl acetate (EA) for extraction. The organic phase was separated, washed sequentially with water and saturated brine, dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography with petroleum ether/ethyl acetate (gradient elution) as eluent to afford the target product indole-3-acetone (2.35 g). The product was analyzed by LC/MS (method LC5): retention time (RT) = 1.56 min; mass-to-charge ratio (m/z) = 174.1 [M + H]+.

75-16-1
280 suppliers
$12.00/10ml

132922-37-3
31 suppliers
$45.00/10mg

1201-26-9
138 suppliers
$80.00/250mg

Yield:1201-26-9 2.35 g

Reaction Conditions:

in tetrahydrofuran at 0; for 5 h;

Steps:

a Intermediate 20. 6-Bromo-8-iodo-1,3-dimethyl-9H-pyrido[3,4-b]indole

a) 1-(1H-Indol-3-yl)propan-2-one Under argon 2-(1H-indol-3-yl)-N-methoxy-N-methylacetamide (3.00 g, 13.75mmol) was dissolved in THF (60 ml) and the solution cooled to 0 °C. A methylmagnesium bromide solution in THF(27.49 ml, 27.49 mmol) was slowly added with stirring. After 2 h a second portion of methylmagnesium bromidesolution (27.49 ml, 27.49 mmol) and after 3 h a third portion of methylmagnesium bromide solution (27.49 ml, 27.49mmol) were added. Then an aqueous ammonium chloride solution was added, followed by EA. The phases wereseparated, and the organic phase was washed with water and brine, dried, filtered and concentrated in vacuo. Theresidue was purified by chromatography over silica gel with HEP/EA (gradient) to yield 2.35 g of the title compound.LC/MS (Method LC5): RT = 1.56 min; m/z = 174.1 [M+H]+

References:

EP3318563,2018,A1 Location in patent:Paragraph 0155