Triisopropyl borate → HCID 86634553, compound
Reaction equation
[B:1](OC(C)C)([O:6]C(C)C)[O:2]C(C)C.Br[C:15]1[CH:16]=[C:17]([NH:22][S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])[C:18]([Cl:21])=[N:19][CH:20]=1.C([Li])CCC>C1COCC1>[Cl:21][C:18]1[N:19]=[CH:20][C:15]([B:1]([OH:6])[OH:2])=[CH:16][C:17]=1[NH:22][S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:25])=[O:24]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Triisopropyl borate (5.69 ml, 24.7 mmol) is added to a solution of N-(5-Bromo-2-chloro-pyridin-3-yl)-benzenesulfonamide (1 g, 2.87 mmol) in anhydrous THF (25 ml) under argon, and the resulting solution is cooled to −78° C. A 1.6 M solution of n-butyl lithium in hexanes (5.39 ml, 8.63 mmol) is added dropwise keeping the temperature below −70° C. The reaction is stirred at −78° C. for 50 minutes. The reaction is quenched with sat. aq. NaCl (20 ml) at −78° C. and then allowed to warm to room temperature and washed with EtOAc. The aqueous layer is concentrated in vacuo, and the residue is dissolved in 2.5M HCl, and the product is extracted into EtOAc, dried (MgSO4) and concentrated in vacuo to yield the title compound as a yellow oil. [M+H]+ 313.
Workup
- customthe temperature below −70° C
- customThe reaction is quenched with sat. aq. NaCl (20 ml) at −78° C.
- temperatureto warm to room temperature
- washwashed with EtOAc
- concentrationThe aqueous layer is concentrated in vacuo
- dissolutionthe residue is dissolved in 2.5M HCl
- extractionthe product is extracted into EtOAc
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-12cebc892b7c4ec8a78b8bb016e75867
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846687B2
Reaction notes
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