Sodium Carbonate → HCID 57750967, compound

HRID 2283286Notes

Reaction equation

HRID 2283286 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.Br[C:13]1[CH:14]=[C:15]([S:19]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[S:29]([NH2:32])(=[O:31])=[O:30])(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.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>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:13]1[CH:14]=[C:15]([S:19]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[S:29]([NH2:32])(=[O:30])=[O:31])(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27346612,3-Dichlorobenzeneboronic acidHCID 57751032HCID 57751032, compound

Product 1

HCID 57750967HCID 57750967, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (14 mg, 0.012 mmol), was added to a solution of 2,3-dichlorophenylboronic acid (57 mg, 0.30 mmol) and 2-[(3-bromophenyl)-sulfonylamino]benzenesulfonamide (97 mg, 0.25 mmol) in DMF (1 mL). The reaction mixture was stirred at RT under argon for 15 minutes before addition of 2M Na2CO3 (0.5 mL). The reaction was stirred overnight at 90° C., filtered and purified by preparative HPLC (XTerra MS C8 column, acetonitrile/ammonium acetate buffer) to give the title compound (61 mg, 53%) as a white solid.

Workup

  1. filtrationfiltered
  2. custompurified by preparative HPLC (XTerra MS C8 column, acetonitrile/ammonium acetate buffer)

Sources & evidence

ORD record
ord-5095e419e99c4985abdbfb2a8089597e
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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