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. 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 HCl (2 M, 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 HCl (2 M, 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-93d4d4b47c814b11852348a4b03cac92
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08357710B2
Reaction notes
Loading…