Triisopropyl borate → (2-(N-(tert-Butyl)sulfamoyl)-5-isobutylthiophen-3-yl)boronic acid
Reaction equation
[CH2:1]([C:5]1[S:9][C:8]([S:10]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])=[O:11])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[Li]CCCC.C([O:26][B:27](OC(C)C)[O:28]C(C)C)(C)C>C1COCC1>[CH2:1]([C:5]1[S:9][C:8]([S:10]([NH:13][C:14]([CH3:15])([CH3:17])[CH3:16])(=[O:12])=[O:11])=[C:7]([B:27]([OH:28])[OH:26])[CH:6]=1)[CH:2]([CH3:4])[CH3:3]Participants
5
Conditions
- Temperature
- -20 °C
Procedure
5-iso-Butyl-N-tert-butylthiophene-2-sulfonamide (10.6 g, 0.039 mol, see step (b) above) was dissolved in THF (165 mL) under N2 and then cooled to −78° C. n-BuLi (1.6 M, 60.19 mL, 0.096 mol) was added via a syringe. The reaction mixture was stirred at −20° C. for 4 h. The tri-iso-propylborate (13.3 mL, 0.058 mol) was then added via a syringe and the reaction mixture was stirred overnight at room temperature. The reaction was quenched with 2 M HCl (20 mL). The organic phase was separated and the water phase was extracted with EtOAc (3×100 mL). The combined organic phase was washed with brine, dried and concentrated in vacuo. The product was used without further purification.
Workup
- additionwas added via a syringe
- stirringthe reaction mixture was stirred overnight at room temperature
- customThe reaction was quenched with 2 M HCl (20 mL)
- customThe organic phase was separated
- extractionthe water phase was extracted with EtOAc (3×100 mL)
- washThe combined organic phase was washed with brine
- customdried
- concentrationconcentrated in vacuo
- customThe product was used without further purification
Sources & evidence
- ORD record
- ord-b82d6fd6773c4d4c9589843c55577ab0
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652054B2
Reaction notes
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