Perfluoro-1-butanesulfonyl fluoride → 3-(Nonafluorobutane-1-sulfonyloxy)-thieno[2,3-c]pyridine-2-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:14][C:9]2=[CH:10][N:11]=[CH:12][CH:13]=[C:8]2[C:7]=1[OH:15])=[O:5])[CH3:2].CCN(C(C)C)C(C)C.[F:25][C:26]([F:41])([C:37]([F:40])([F:39])[F:38])[C:27]([F:36])([F:35])[C:28]([F:34])([F:33])[S:29](F)(=[O:31])=[O:30]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[S:14][C:9]2=[CH:10][N:11]=[CH:12][CH:13]=[C:8]2[C:7]=1[O:15][S:29]([C:28]([F:33])([F:34])[C:27]([F:35])([F:36])[C:26]([F:25])([F:41])[C:37]([F:40])([F:39])[F:38])(=[O:31])=[O:30])=[O:5])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of 3-hydroxy-thieno[2,3-c]pyridine-2-carboxylic acid ethyl ester-(950 mg, 4.26 mmol) and DMAP (26 mg, 0.21 mmol) in DCM (12 ml) at 0° C. was added DIPEA (1.8 ml, 10.2 mmol) and nonafluorobutylsulfonyl fluoride (0.99 ml, 5.53 mmol). After 10 minutes the reaction mixture was warmed to room temperature and stirred for an additional 20 hours. The reaction mixture was diluted with DCM (30 ml) and washed with water (20 ml). The organic phase was dried over sodium sulphate, filtered and evaporated to give a yellow oil. The oil was purified by flash chromatography (Si-SPE, pentane:diethyl ether, gradient 90:10 to 65:35) to afford the title compound as a colourless oil which crystallised on standing (678 mg, 31%): LCMS (method B). RT=4.49 min, M+H+=508.
Workup
- washwashed with water (20 ml)
- dry with materialThe organic phase was dried over sodium sulphate
- filtrationfiltered
- customevaporated
- customto give a yellow oil
- customThe oil was purified by flash chromatography (Si-SPE, pentane:diethyl ether, gradient 90:10 to 65:35)
Sources & evidence
- ORD record
- ord-51b6027be16940d3b31a7da3f4992b55
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893085B2
Reaction notes
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