3-CYANO-5-METHOXY-2-METHYLINDOLE synthesis

5synthesis methods

Product Name:3-CYANO-5-METHOXY-2-METHYLINDOLE
CAS Number:481668-37-5
Molecular formula:C11H10N2O
Molecular Weight:186.21

5-METHOXY-2-METHYL-1H-INDOLE-3-CARBALDEHYDE

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Yield: 50%

Reaction Conditions:

with aluminum (III) chloride;sodium azide in tetrahydrofuran for 8 h;Reflux;

Steps:

Typical procedure for the preparation of substituted 2-methylindole-3-carbonitriles (8a-8h)
General procedure: To a solution of AlCl₃ (2.67 g, 20.0 mmol) in THF (100 mL), NaN₃(3.90 g, 60.0 mmol)and corresponding substituted 2-methylindole-3-carboxadehyde 7 (10.0 mmol) were added. The reaction mixture was heated at reflux for 8 hours. The solvent was then removed under reduced pressure, and the residue was diluted with 10% HCl (20 mL). This mixture was extracted with CH₂Cl₂(2 X 60 mL). The combined organic layer was dried over Na₂SO₄ and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (EtOAc/hexanes = 1:3) to obtain the corresponding carbonitrile.

References:

Thanetchaiyakup, Adisak;Rattanarat, Hassayaporn;Chuanopparat, Nutthawat;Ngernmeesri, Paiboon [Tetrahedron Letters,2018,vol. 59,# 11,p. 1014 - 1018] Location in patent:supporting information

1076-74-0 Synthesis