Sodium Carbonate → HCID 57750907, compound

HRID 2283350Notes

Reaction equation

HRID 2283350 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[S:10]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[S:20]([NH2:23])(=[O:22])=[O:21])(=[O:12])=[O:11])=[CH:4][CH:3]=1.[C:24]1(B(O)O)[CH2:28][CH2:27][CH2:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O1CCCC1.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:24]1([C:2]2[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[S:10]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[S:20]([NH2:23])(=[O:22])=[O:21])(=[O:12])=[O:11])=[CH:4][CH:3]=2)[CH2:28][CH2:27][CH2:26][CH:25]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 3861343(Cyclopent-1-en-1-yl)boronic acidHCID 42644851HCID 42644851, compound

Product 1

HCID 57750907HCID 57750907, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

2-[[(E)-2-(4-Bromophenyl)ethenylsulfonylamino]benzenesulfonamide (75 mg, 0.18 mmol), cyclopenten-1-ylboronic acid (40.2 mg, 0.36 mmol), (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (14.79 mg, 0.02 mmol) and sodium carbonate (38.1 mg, 0.36 mmol) were suspended in N,N-dimethylformamide (2 mL) and the reaction mixture was stirred under an atmosphere of argon at 90° C. for 16 hours. The reaction mixture was diluted with tetrahydrofuran and filtered through Celite. The solvent was removed in vacuo and the residue was purified by preparative HPLC. The residue was purified a second time by column chromatography, using gradient mixtures of ethyl acetate/heptane as eluent (0%-100% ethyl acetate) to give 50 mg (69% yield) of the title compound.

Workup

  1. filtrationfiltered through Celite
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by preparative HPLC
  4. customThe residue was purified a second time by column chromatography

Sources & evidence

ORD record
ord-f5b6d663531f437aae4d6cb4437487a2
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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