1-Ethynyl-3-(propylsulfonyl)benzene → Tert-butyl(4-fluoro-2-{[3-(propylsulfonyl)phenyl]ethynyl}phenoxy)acetate
Reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH2:12][CH3:13])(=[O:10])=[O:9])=[CH:4][C:3]=1[C:14]#[C:15][Si](C)(C)C.[C:20]([O:24][C:25](=[O:36])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=1Br)([CH3:23])([CH3:22])[CH3:21].C(C1C=CC=C(S(CCC)(=O)=O)C=1)#C>>[C:20]([O:24][C:25](=[O:36])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=1[C:15]#[C:14][C:3]1[CH:2]=[CH:7][CH:6]=[C:5]([S:8]([CH2:11][CH2:12][CH3:13])(=[O:10])=[O:9])[CH:4]=1)([CH3:23])([CH3:21])[CH3:22]Participants
4
Procedure
Following the general method as outlined in Intermediate 107, starting from tert-butyl(2-bromo-4-fluorophenoxy)acetate (Intermediate 119) and 1-ethynyl-3-(propane-1-sulfonyl)-benzene (Intermediate 42), the title compound was obtained as a yellow sticky solid after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.
Sources & evidence
- ORD record
- ord-3877c77a4b18407f9b281d6f14131e62
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273769B2
Reaction notes
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