Cesium carbonate → HCID 69358469, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged under nitrogen with methyl 3-bromo-5-nitrobenzoate (D11) (136 mg, 0.52 mmol, 1,1 equiv), Cs2CO3 (216 mg, 0.66 mmol, 1.4 equiv), tris(dibenzylideneacetone)dipalladium(0) (22 mg, 0.023 mmol, 0.05 equiv), Xantphos (27 mg, 0.047 mmol, 0.1 equiv) and toluene (10 ml). 4-phenyltetrahydro-2H-1,2-thiazine 1,1-dioxide (J. Morris, D. G. Wishka J. Org. Chem. 1991, 56, 3549-3556, 100 mg, 0.47 mmol, 1 equiv) was then added and the resulting mixture was stirred at 120° C. for 5 h then cooled to room temperature and concentrated in vacuo. The residue was partitioned between H2O and AcOEt and the aqueous phase was re-extracted with AcOEt. The combined organic solutions were dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (iso-hexane/AcOEt: 7/3) gave methyl 3-(1,1-dioxido-4-phenyltetrahydro-2H-1,2-thiazin-2-yl)-5-nitrobenzoate (B123) (110 mg, 60%) as a yellow oil. [M+H+ NH3]+=408.3, RT=3.24 min

Provenance & Evidence