Trifluoromethanesulfonic anhydride → HCID 118162075, compound
Reaction equation
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([NH:10][C:11](=O)[CH3:12])[CH:7]=[CH:8][CH:9]=1)#[N:2].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C[Si]([N:33]=[N+:34]=[N-:35])(C)C.[Cl-].N>C(#N)C>[CH3:12][C:11]1[N:10]([C:6]2[CH:5]=[C:4]([CH2:3][C:1]#[N:2])[CH:9]=[CH:8][CH:7]=2)[N:35]=[N:34][N:33]=1Participants
Procedure
To a solution of N-(3-cyanomethyl-phenyl)-acetamide (500 mg, 2.87 mmol) in anhydrous acetonitrile (5 mL) was added trifluoromethanesulfonic anhydride (1.62 g, 5.74 mmol) slowly at −5° C. The resulting mixture was stirred for 5 min, trimethylsilylazide (1.32 g, 11.48 mmol) was added slowly keeping the temperature below −5° C. The resulting mixture was stirred at −5° C. for 1 h. The reaction was poured into cooled aqueous ammonia chloride and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate and concentrated to give the crude product, which was purified by silica gel column chromatography (1-2% MeOH in DCM) to afford the title compound (260 mg, 1.31 mmol, 45% yield) as a yellow solid. MS (ESI) m/z 199.9 [M+H]+.
Workup
- customthe temperature below −5° C
- stirringThe resulting mixture was stirred at −5° C. for 1 h
- additionThe reaction was poured
- extractionextracted with ethyl acetate three times
- dry with materialThe combined organic layers were dried over sodium sulfate
- concentrationconcentrated
- customto give the crude product, which
- customwas purified by silica gel column chromatography (1-2% MeOH in DCM)
Sources & evidence
- ORD record
- ord-504d56d0bd944431a8e39e6d9d94b610
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156798B2
Reaction notes
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