Sodium Carbonate → HCID 25012075, compound

HRID 1924117Notes

Reaction equation

HRID 1924117 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][N:14]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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>[N:16]1[CH:17]=[CH:18][C:13]([CH2:12][NH:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([C:23]3[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=3)=[CH:3][CH:4]=2)(=[O:10])=[O:9])=[N:14][CH:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 25012074HCID 25012074, compound

Product 1

HCID 25012075HCID 25012075, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

The sulphonamide from example 2 (1.0 eq), 4-fluorophenylboronic acid and Pd(PPh3)4 were dissolved in dioxane (3 mL/mmol) and an aqueous solution of sodium carbonate (2 mL/mmol) was added. The reaction mixture was heated under reflux overnight and after completion of the reaction the solvent was removed under reduced pressure. The residue was purified by chromatography to yield the title compound as beige solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. customafter completion of the reaction the solvent
  4. customwas removed under reduced pressure
  5. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-6a9aae894f8548e28e6bd8320fe035dc
Source dataset
uspto-grants-2012_05
Patent number
US08178540B2

Reaction notes

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