Triisopropyl borate → 5-Butyl-2-(N-tert-butylaminosulfonyl)thiophene-3-boronic acid
Reaction equation
[C:1]([NH:5][S:6]([C:9]1[S:10][C:11]([CH2:14][CH2:15][CH2:16][CH3:17])=[CH:12][CH:13]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.C([O:26][B:27](OC(C)C)[O:28]C(C)C)(C)C>C1COCC1>[CH2:14]([C:11]1[S:10][C:9]([S:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:7])=[O:8])=[C:13]([B:27]([OH:28])[OH:26])[CH:12]=1)[CH2:15][CH2:16][CH3:17]Participants
5
Conditions
- Temperature
- -20 °C
Procedure
5-Butylthiophene-2-sulfonic acid tert-butylamide (2.9 g, 0.010 mol, see step (a) above) was dissolved in THF (40 mL) under N2 and then cooled to −78° C. n-BuLi (1.6 M, 16.2 mL, 0.026 mol) was added via a syringe. The reaction mixture was stirred at −20° C. for 4 hours. 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 and dried and concentrated in vacuo. The product was used in the next step 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 in the next step without further purification
Sources & evidence
- ORD record
- ord-7022f49914564e9c9bdfc2027f6ba44a
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652054B2
Reaction notes
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