2-Aminothiazole → Ethyl hexanoate

Participants

Reaction Conditions

Reaction Steps

In a dry pressure bottle, 3-[5-bromo-3-(1,4-dimethyl-1H-indol-3-ylmethyl) 2-oxo-2,3-dihydro-benzoimidazol-1-yl]-hexanoic acid ethyl ester (200 mg, 0.390 mmol) was dissolved in 50% Toluene/NMP (10 ml). To the solution, 2-amino thiazole (59 mg, 0.585 mmol), Cesium carbonate (191 mg, 0.585 mmol), 2(dicyclohexylphosphino)biphenyl (14 mg, 0.040 mmo), tris (dibenzyledeneacetone)-dipalladium (0) 99 mg, 0.010 nmol) were added. The bottle was then purged for 5 minutes by passing a slow stream of argon through the mixture while stirring. As the bottle was ready to be capped, the argon flow was increased. After capping, the reaction vessel was then immersed in an oil bath heated to 100° C. for 18 hours. An aliquout was removed and checked by TLC. The cooled reaction mixture was then diluted with Ethyl Acetate (200 ml) and washed with water 3 times. The organic phase was again washed with 1N HCl (200 ml), followed with brine. The collected organic phase was dried over MgSO4, filtered and evaporated to dryness to give an oil, which was purified by flash Chromatography, eluded with 30% to 50% ethyl acetate in Hexanes in 30 minutes to give 205 mg (35%) of 3-[3-1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-5-phenylamino-2,3-dihydro-benzoimidazol-1-yl]hexanoic acid Ethyl ester. LCMS (ESMS): m/z 524.65 (M+H).

Provenance & Evidence