2,4-Difluorobenzenesulfonyl Chloride → 2,4-difluoro-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide
Reaction equation
[CH3:1][O:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)=[CH:5][N:4]=1.[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[S:27](Cl)(=[O:29])=[O:28]>N1C=CC=CC=1>[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[S:27]([NH:9][C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[C:6]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)[CH:7]=1)(=[O:29])=[O:28]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To the solution of 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine (400 mg, 1.6 mmol) in pyridine (5 mL) was added 2,4-difluorobenzenesulfonyl chloride (407 mg, 1.9 mmol) slowly, the reaction mixture was stirred at room temperature overnight, the solvent was evaporated in vacuo, and the residue was treated with brine (5 mL) and extracted with EtOAc (3×10 mL). The combined organic layer was evaporated in vacuo, and the residue was purified by column chromatography using petroleum ether:EtOAc=5:1 as eluent to afford the desired product 2,4-difluoro-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide as white solid in 59% yield (400 mg). m/z 427 (M+H)+.
Workup
- customthe solvent was evaporated in vacuo
- additionthe residue was treated with brine (5 mL)
- extractionextracted with EtOAc (3×10 mL)
- customThe combined organic layer was evaporated in vacuo
- customthe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-6ef3e80fc9794d25af7b500c3dafda8a
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181264B2
Reaction notes
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