1-(cyanomethyl)-1H-indole-2-carboxylic acid synthesis

Yield:959089-89-5 70%

Reaction Conditions:

Stage #1: 1-(cyanomethyl)indole-2-carboxylic acid ethyl esterwith lithium hydroxide in tetrahydrofuran;water at 20; for 6 h;
Stage #2: in tetrahydrofuran;water; pH=2;

Steps:

44 Cyanomethyl-1H-indole-2-carboxylic acid

To a solution of 1.0 eq. of 1-cyanomethyl-1H-indole-2-carboxylic acid ethyl ester, in a mixture of THF/H₂O ((9/1) was added LiOH.H₂O (1.0 eq.) and the reaction mixture stirred 6 h at RT, acidified to pH2 and then partially concentrated until precipitation of the crude product which was filtered off and washed with Et₂O and then dried to give the desired product as a light yellow solid (70%). ES-MS m/e (%): 199.0 (M-H⁺).

References:

US2008/139548,2008,A1 Location in patent:Page/Page column 22