Potassium Phosphate, Tribasic → 3-(2-Chloro-4-methylsulfanyl-phenylamino)-1-methyl-1H-indole-2-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

3-Amino-1-methyl-1H-indole-2-carboxylic acid ethyl ester (200 mg, 0.91 mmol) and 1-bromo-2-chloro-4-methylsulfanyl-benzene (304 mg, 1.28 mmol) were dissolved in toluene (5 ml) and Pd2(dba)3 (42 mg, 0.05 mmol) was added, followed by Xantphos (53 mg, 0.09 mmol) and potassium phosphate tribasic (386 mg, 1.82 mmol). The mixture was degassed and purged with argon, then stirred under argon at 120° C. for 16 hours. After cooling, the mixture was filtered through celite then concentrated. Purification of the resultant residue by flash chromatography (Si-PCC, ether:pentane gradient 1:4 to 1:0) gave the title compound as a yellow oil (300 mg, 88%). LCMS (method B): RT=2.64, M+H+ 376/378.

Provenance & Evidence