Dichloromethane → 4'-Bromo-N-(tert-butyl)-3'-fluoro-[1,1'-biphenyl]-2-sulfonamide

HRID 1523942Notes

Reaction equation

HRID 1523942 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[F:9].[C:10]([NH:14][S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O)(=[O:17])=[O:16])([CH3:13])([CH3:12])[CH3:11].C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl>C(OCC)(=O)C.O.O1CCOCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:19]2[C:18]([S:15]([NH:14][C:10]([CH3:13])([CH3:12])[CH3:11])(=[O:16])=[O:17])=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:4][C:3]=1[F:9]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27250061-Bromo-2-fluoro-4-iodobenzeneHCID 4997616Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-

Product 1

HCID 903130764'-Bromo-N-(tert-butyl)-3'-fluoro-[1,1'-biphenyl]-2-sulfonamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

1-Bromo-2-fluoro-4-iodobenzene (117 mg, 0.389 mmol) and (2-(N-(tert-butyl)sulfamoyl)phenyl) boronic acid (100 mg, 0.389 mmol) were added to a 5 mL sealable vial equipped with a stir bar. 1,4-Dioxane (1 mL) and 2 M Na2CO3 (1 mL) solution were added. Argon was bubbled through the solvent while it was rapidly stirred for 10 min then Pd(dppf)Cl2.CH2Cl2 (14 mg, 0.019 mmol) was added. The mixture was then stirred for 15 hours at 80° Celsius under an argon atmosphere. The reaction was diluted with 2 mL of ethyl acetate and 2 mL of water and the aqueous layer was extracted with ethyl acetate (3×10 mL). The combined organic extracts were then dried with Na2SO4 and concentrated to dryness. The crude product was purified by FCC to give the title compound. 1H NMR (500 MHz, CDCl3) δ 8.20-8.15 (dd, J=7.9, 1.4, 1H), 7.64-7.59 (dd, J=8.2, 7.1, 1H), 7.60-7.55 (m, 1H), 7.54-7.49 (m, 1H), 7.31-7.27 (m, 2H), 7.21-7.16 (dd, J=8.5, 2.2, 1H), 3.65 (s, 1H), 1.07 (s, 9H).

Workup

  1. customequipped with a stir bar
  2. customArgon was bubbled through the solvent while it
  3. stirringThe mixture was then stirred for 15 hours at 80° Celsius under an argon atmosphere
  4. extractionthe aqueous layer was extracted with ethyl acetate (3×10 mL)
  5. dry with materialThe combined organic extracts were then dried with Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe crude product was purified by FCC

Sources & evidence

ORD record
ord-7fa829300e974c098260ece6509fd007
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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