ChemicalBook CAS DataBase List AKOS B006681

AKOS B006681 synthesis

6synthesis methods

Product Name:AKOS B006681
CAS Number:1204-32-6
Molecular formula:C11H11NO2
Molecular Weight:189.21

50820-65-0
234 suppliers
$6.00/1g

74-88-4
341 suppliers
$15.00/10g

1204-32-6
70 suppliers
$10.00/250mg

Yield: 100%

Reaction Conditions:

Stage #1:indole-6-carboxylic acid methyl ester with sodium hydride in N,N-dimethyl-formamide at 20; for 0.5 h;
Stage #2:methyl iodide in N,N-dimethyl-formamide at 20; for 20 h;

Steps:

20
To a stirred solution of methyl 1 H-indole-6-carboxylate (0.76g, 4.34mmol) in DMF (10ml) at room temperature was added sodium hydride (0.35g, 8.75mmol). The resultant suspension was stirred for 30min at room temperature followed by the addition of methyl iodide (0.54ml, 8.67mmol). The reaction mixture was stirred for 2Oh at room temperature and was then quenched by the addition of water (20ml) and ethyl acetate (20ml). The aqueous layer was extracted with ethyl acetate (3 x 30ml) and the combined extracts were dried with a phase separating column. The solvent was then removed in vacuo to give the desired product as an off-white solid (0.85g, 100%). LC-MS (Acidic) (MH⁺=I 90). The product was used without further purification

References:

GLAXO GROUP LIMITED WO2009/71577, 2009, A1 Location in patent:Page/Page column 43