Methyl Acrylate → (+/-)-tert-Butyl 4-(2-(5-cyanobenzo[d]oxazol-2-yl)-5-methoxy-5-oxopentan-2-yl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

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Reaction Steps

To a mixture of potassium tert-butoxide (15.60 mg, 0.139 mmol) in THF (329 μl) at −78° C. under nitrogen was added (±)-tert-butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)ethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 150-A) (50 mg, 0.116 mmol) in THF (659 μL). After stirring for 5 min a solution of 18-crown-6 (3.06 mg, 0.012 mmol) in THF (412 μl) that was degassed and placed under nitrogen was added to the mixture at the same temperature and stirred for another 5 min. Then a solution of methyl acrylate (210 μl, 2.318 mmol) in THF (329 μl) was degassed and added dropwise and stirred at the same temp for 30 min. The reaction mixture was allowed to reach rt over 1 hr and then was stirred at rt for 30 hrs. The reaction mixture was quenched with a saturated solution of ammonium chloride, diluted with DCM and water, passed through a phase separator and concentrated to give the title compound that was taken to the next step without further purification. MS (ESI+) m/z 518.5 (M+H).

Provenance & Evidence