Methyl 2-Bromo-3-cyclohexyl-6-indolecarboxylate synthesis

7synthesis methods

Product Name:Methyl 2-Bromo-3-cyclohexyl-6-indolecarboxylate
CAS Number:494799-19-8
Molecular formula:C16H18BrNO2
Molecular Weight:336.22

494799-18-7 Synthesis

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

494799-18-7
17 suppliers
inquiry

Methyl 2-Bromo-3-cyclohexyl-6-indolecarboxylate

494799-19-8
30 suppliers
inquiry

Yield:494799-19-8 86%

Reaction Conditions:

with pyridinium hydrobromide perbromide in tetrahydrofuran;chloroform at 0 - 20; for 2 h;

Steps:

Methyl 2-bromo-3-cyclohexyl-2-1H-indole-6-carboxylate; Dry pyridinium tribromide (12.0 g, 38 mmol) was added in one portion to a stirred and cooled (ice/water bath) solution of methyl 3-cyclohexyl-1H-indole-6-carboxylate (7.71 g, 30 mmol) in a mixture of THF (80 mL) and chloroform (80 mL). The flask was removed from the cooling bath and stirring was continued for 2 hours at room temperature. The mixture was sequentially washed with 1M NaHSO₃(2×50 mL) and 1N HCl (50 mL). It was then dried over anhydrous sodium sulfate, filtered, and concentrated. The concentrate was treated with hexanes and the resulting precipitate was collected by filtration to provide the desired product as an off-white solid (5.8 g, 58%). ¹H NMR (300 MHz, CDCl₃) δ 1.38 (m, 3H), 1.85 (m, 7H), 2.81 (m, 1H), 7.71 (m, 2H), 8.03 (s, 1H), 8.47 (s, 1H).

References:

US2007/78122,2007,A1 Location in patent:Page/Page column 175

494799-18-7 Synthesis

494799-18-7
17 suppliers
inquiry