3-CYCLOHEXYL-1H-INDOLE-6-CARBOXYLIC ACID METHYL ESTER synthesis

11synthesis methods

Product Name:3-CYCLOHEXYL-1H-INDOLE-6-CARBOXYLIC ACID METHYL ESTER
CAS Number:494799-18-7
Molecular formula:C16H19NO2
Molecular Weight:257.33

494799-17-6
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67-56-1 Synthesis

67-56-1
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3-CYCLOHEXYL-1H-INDOLE-6-CARBOXYLIC ACID METHYL ESTER

494799-18-7
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Yield:494799-18-7 100%

Reaction Conditions:

with thionyl chloride at 0; for 24 h;Heating / reflux;

Steps:

1.2

Step 2; methy 3-cvclohexyl-1H-indole-6-carboxylate; A solution (0.5 M) of 3-cyclohexenyl-1H-indole-6-carboxylic acid (from Step 1) in THF/M eOH (0.5 M, 1:1, v/v) was hydrogenated for 14 h over Pd(OH)2/C (0.1 eq., 20%) at 60 psi. The catalyst was removed by filtration on a pad of celite and the filtrate evaporated to dryness to afford 3-cyclohexyl-1 H-indoIe-6-carboxylic acid (90%) as a white solid 1H NMR (300 MHz, DMSO-d6, 300 K) 6 1.20 -1.53 (m, SH), L70-L87 (m, 3H), 1.90-2.02 (m, 2H), 2.69-2.86 (m, 1H), 7.40 (s, 1H), 7.55-7.65 (rn, 2H), 8.0 (s, 1H), 11.40 (s, 1H); MS (ES+ m/z 244 (M+H)+. A solution of the foregoing compound in MeOH {0.4 M) was treated at 0 °C with thionylchloride (0.5 eq.) and refluxed for 24 h. Volatiles were removed under vacuum to afford the title compound (100%) as a solid.

References:

WO2006/29912,2006,A1 Location in patent:Page/Page column 21-22

494799-17-6
53 suppliers
$52.50/250mg