ChemicalBook CAS DataBase List methyl indoline-5-carboxylate

methyl indoline-5-carboxylate synthesis

6synthesis methods

Product Name:methyl indoline-5-carboxylate
CAS Number:141452-01-9
Molecular formula:C10H11NO2
Molecular Weight:177.2

1011-65-0

141452-01-9

The general procedure for the synthesis of indoline-5-carboxylic acid methyl ester from indole-5-carboxylic acid was as follows: to a 10 mL solution of 1H-indole-5-carboxylic acid methyl ester (1 g, 5.71 mmol) in acetic acid was slowly added sodium cyano-borohydride (1.08 g, 17.18 mmol) at 0 °C, with the addition time being controlled to be within 5 minutes. The reaction mixture was stirred at room temperature for 1 hour. Upon completion of the reaction, water (3 mL) was added and all solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate (150 mL) and saturated sodium bicarbonate solution (150 mL) for liquid-liquid separation. The aqueous phase was further extracted with ethyl acetate (3 x 75 mL). All organic phases were combined, washed with saturated saline (150 mL), dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The crude product was purified by fast column chromatography (eluent: 0-50% hexane solution of ethyl acetate containing 0.1% triethylamine) to afford the target product methyl indoline-5-carboxylate (0.99 g, 99% yield).

1011-65-0
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$6.00/250mg

141452-01-9
109 suppliers
$16.00/100mg

Yield: 99%

Reaction Conditions:

with sodium cyanoborohydride;acetic acid at 0 - 20; for 1.08333 h;

Steps:

19.A
To a solution of lH-Indole-5-carboxylic acid methyl ester (1 g, 5.71 mmol) in 10 mL of acetic acid at 0 ⁰C, was added sodium cyanoborohydride (1.08 g, 17.18 mmol) over 5 minutes. The mixture was stirred at room temperature for Ih. Water (3 mL) was added and all the solvents were removed under vacuum. The residue was dissolved in ethyl acetate (150 mL) and saturated NaHCCh (150 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (3 x 75 mL). The combined extracts were washed with brine (150 mL), dried, filtered and evaporated. The residue was purified by flash chromatography (0-50% ethyl acetate in hexane + 0.1% triethylamine) to afford 0.99 g (99%) of 19a.

References:

BOEHRINGER INGELHEIM INTERNATIONAL GMBH;NEUROCRINE BIOSCIENCES, INC.;TRAN, Joe, A.;CHEN, Chen WO2010/149685, 2010, A1 Location in patent:Page/Page column 51