Cesium carbonate → HCID 66802732, compound
Reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S(O[CH2:24][C:25]([F:28])([F:27])[F:26])(=O)=O>CN(C=O)C.CCOC(C)=O>[CH3:11][O:10][C:8]([C:5]1[CH:4]=[CH:3][C:2]([NH:1][CH2:24][C:25]([F:28])([F:27])[F:26])=[CH:7][N:6]=1)=[O:9]Participants
Procedure
Methyl 5-aminopyridine-2-carboxylate (Intermediate 168, 200 mg, 1.31 mmol) and cesium carbonate (642 mg, 1.97 mmol) were dissolved in anhydrous DMF (2 mL) and stirred under nitrogen for 10 min. 2,2,2-Trifluoroethyl trifluoromethanesulfonate (246 μL, 1.70 mmol) was added and the mixture was stirred at room temperature for 18 h. Further cesium carbonate (642 mg, 1.97 mmol) and 2,2,2-trifluoroethyl trifluoromethanesulfonate (246 μL, 1.70 mmol) were added and the mixture was stirred at 85 C for 6 h. The mixture was diluted with EtOAc (50 mL) and washed with water (3×20 mL), then brine (20 mL) and then dried over sodium sulfate and evaporated under vacuum. The crude residue was purified by flash chromatography (0-10% EtOAc in heptane) to afford the title compound as a white solid (75 mg, 24%). Method B HPLC-MS: MH+ requires m/z=235. Found: m/z=235, Rt=1.76 min (84%).
Workup
- stirringthe mixture was stirred at room temperature for 18 h
- stirringthe mixture was stirred at 85 C for 6 h
- washwashed with water (3×20 mL)
- dry with materialbrine (20 mL) and then dried over sodium sulfate
- customevaporated under vacuum
- customThe crude residue was purified by flash chromatography (0-10% EtOAc in heptane)
Sources & evidence
- ORD record
- ord-068141d451ec4838a406f2a92451bb99
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895733B2
Reaction notes
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