2,5-Dichlorobenzenesulfonyl chloride → HCID 86678948, compound

HRID 706772Notes

Reaction equation

HRID 706772 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:6]=[CH:5][C:3]=1[NH2:4].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=1[S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl.N1C=CC=CC=1>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=1[S:26]([NH:4][C:3]1[CH:5]=[CH:6][C:7]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)=[CH:8][C:2]=1[F:1])(=[O:28])=[O:27]

Participants

5

Reactant 2

HCID 794012,5-Dichlorobenzenesulfonyl chlorideHCID 179061722-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 86678948HCID 86678948, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.5 g of 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline in 17 ml DCM and 0.5 ml pyridine, 1.5 g of 2,5-dichloro-benzenesulfonyl chloride were added, and the reaction mixture was stirred for 16 h at RT. Then the solvents were removed under reduced pressure and the crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/EtOAc. The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 2.2 g.

Workup

  1. customThen the solvents were removed under reduced pressure
  2. customthe crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/EtOAc
  3. additionThe fractions containing the product
  4. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-ed2b033449a340e3bdd523636f478b5d
Source dataset
uspto-grants-2015_11
Patent number
US09174993B2

Reaction notes

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