Dichloromethane → HCID 90313155, compound

HRID 1523743Notes

Reaction equation

HRID 1523743 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[F:9].[CH3:10][NH:11][S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O)(=[O:14])=[O:13].C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl>O.O1CCOCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:16]2[C:15]([S:12]([NH:11][CH3:10])(=[O:13])=[O:14])=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:4][C:3]=1[F:9]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27250061-Bromo-2-fluoro-4-iodobenzeneHCID 46739029[2-(Methylsulfamoyl)phenyl]boronic acid

Product 1

HCID 90313155HCID 90313155, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1-Bromo-2-fluoro-4-iodobenzene (6.30 g, 20.9 mmol) and (2-(N-methyl-sulfamoyl)-phenyl)boronic acid (4.50 g, 20.9 mmol) were added to a 250 mL flask equipped with a stir bar and reflux condenser. 1,4-Dioxane (50 mL) and Na2CO3 (2 M, 50 mL) were added. Argon was bubbled through the solvent while it was rapidly stirred for 10 minutes before Pd(dppf)Cl2.CH2Cl2 (766 mg, 1.05 mmol) was added and the reaction was stirred at 80° Celsius for 15 hours. The reaction was then diluted with 50 mL of water and extracted with ethyl acetate (1×50 mL, 3×100 mL). The combined organic extracts were dried with Na2CO3, filtered and concentrated to dryness. The crude product was purified by FCC to give 4′-bromo-3′-fluoro-N-methyl-[1,1′-biphenyl]-2-sulfonamide. 1H NMR (500 MHz, CDCl3) δ 8.17-8.11 (m, 1H), 7.66-7.59 (m, 2H), 7.59-7.54 (m, 1H), 7.33-7.29 (m, 1H), 7.28-7.23 (m, 1H), 7.20-7.13 (m, 1H), 3.67-3.56 (dd, J=10.1, 4.5, 1H), 2.46-2.43 (d, J=5.3, 3H).

Workup

  1. customequipped with a stir bar
  2. temperaturereflux condenser
  3. customArgon was bubbled through the solvent while it
  4. stirringthe reaction was stirred at 80° Celsius for 15 hours
  5. extractionextracted with ethyl acetate (1×50 mL, 3×100 mL)
  6. dry with materialThe combined organic extracts were dried with Na2CO3
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe crude product was purified by FCC

Sources & evidence

ORD record
ord-494c22ab4a8b48efaadccae84bfa1b7b
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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