4-Chloro-3-fluorophenylboronic Acid → N-(2,4'-dichloro-3'-fluorobiphenyl-4-yl)methanesulfonamide

HRID 1941761Notes

Reaction equation

HRID 1941761 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][C:3]=1[Cl:13].[Cl:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][C:16]=1[F:24]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[Cl:13][C:3]1[CH:4]=[C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:6]=[CH:7][C:2]=1[C:18]1[CH:19]=[CH:20][C:15]([Cl:14])=[C:16]([F:24])[CH:17]=1

Participants

5

Reactant 2

HCID 27786564-Chloro-3-fluorophenylboronic AcidHCID 22193858N-(4-bromo-3-chlorophenyl)methanesulfonamide

Product 1

HCID 46191051N-(2,4'-dichloro-3'-fluorobiphenyl-4-yl)methanesulfonamide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

N-(4-bromo-3-chlorophenyl)methanesulfonamide (B, 100.0 mg, 0.351 mmol), 4-chloro-3-fluorophenylboronic acid (73.4 mg, 0.421 mmol, L2 equiv.) and Pd(PPh3)4 (20.3 mg, 0.0176 mmol, 0.05 equiv.) was placed in a 50 mL round bottomed flask under a nitrogen atmosphere. To the flask were added 2M-Na1CO3 (1.0 mL, 2.0 mmol, 5.7 equiv.) and DME (4 mL) subsequently at ambient temperature. The mixture was heated under reflux conditions for 1 hours. The mixture was filtered through Celite (3 g) and the Celite was washed with EtOAc (70 mL). The solvent was removed under a reduced pressure. Obtained crude mixture was purified by column chromatography (SiO2=80 g, EtOAc/hexane=1:3˜1:1, Rf=0.4) to give the desired product as colorless crystals (compound 5 (designated PT-017).

Workup

  1. temperatureThe mixture was heated under reflux conditions for 1 hours
  2. filtrationThe mixture was filtered through Celite (3 g)
  3. washthe Celite was washed with EtOAc (70 mL)
  4. customThe solvent was removed under a reduced pressure
  5. customObtained crude mixture
  6. customwas purified by column chromatography (SiO2=80 g, EtOAc/hexane=1:3˜1:1, Rf=0.4)

Sources & evidence

ORD record
ord-0ef032fbd36b45baaf19e2282c78c62b
Source dataset
uspto-grants-2013_03
Patent number
US08389500B2

Reaction notes

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