Potassium Carbonate → HCID 68283204, compound

Participants

Reaction Steps

To a suspension of 3-(pyrrolidin-1-yl)benzoic acid (1.0 g, 5.23 mmol) and K2CO3 1.75 g (12.55 mmol) in DMF (10.8 ml) was added methyl isocyanoacetate (551 mg, 5.23 mmol) in DMF (6.8 mL). The resulting mixture was stirred at rt for 5 min and then cooled to 0° C. A solution of DPPA (1.13 mL, 5.23 mmol) in DMF (6.8 mL) was added dropwise. The resulting mixture was stirred at 0° C. for 2 h and then at rt overnight. It was then diluted with toluene-EtOAc 1:1 (110 mL) and the organic layer was washed with water (55 mL) and aq. sat. NaHCO3-solution (45 mL), dried (MgSO4), filtered and concentrated to dryness. The residue was purified by FC (DCM/MeOH 9:1; Rf=0.41) to afford methyl 5-(3-(pyrrolidin-1-yl)phenyl)oxazole-4-carboxylate as a orange oil. LC-MS conditions A: tR=0.93 min, [M+H]+=273.04.

Provenance & Evidence