Sodium Iodide → Methyl 2-(2-methoxy-4-(spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4'-piperidine]-1'-ylcarbonyl)phenoxy)acetate

Participants

Reaction Conditions

Reaction Steps

To (4-hydroxy-3-methoxyphenyl)(spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-yl)methanone (200 mg, 0.512 mmol), sodium iodide (38.4 mg, 0.256 mmol), Cs2CO3 (334 mg, 1.03 mmol), and DCE (5.0 mL) was added methyl 2-bromoacetate (49 μL, 0.51 mmol). The mixture was stirred at 60° C. for 18 h. Additional methyl 2-bromoacetate (1.0 mmol) was added and the mixture was heated for 3 h at 60° C. The mixture was cooled and then filtered. The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography on silica gel (0-30% ethyl acetate/DCM) to yield methyl 2-(2-methoxy-4-(spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-ylcarbonyl)phenoxy)acetate (140 mg, 59%). ESI-MS m/z calc. 462.2, found 463.5 (M+1)+; Retention time: 2.68 minutes (4 min run).

Provenance & Evidence