Water → HCID 57750982, compound

HRID 2283351Notes

Reaction equation

HRID 2283351 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]([C:28]#[C:29]B(OC(C)C)OC(C)C)([CH3:27])([CH3:26])[CH3:25].C(=O)([O-])[O-].[Na+].[Na+].O>CN(C)C=O.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]>[CH3:25][C:24]([CH3:27])([CH3:26])[C:28]#[C:29][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

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 14117495Dipropan-2-yl (3,3-dimethylbut-1-yn-1-yl)boronateHCID 42644851HCID 42644851, compound

Product 1

HCID 57750982HCID 57750982, compoundYield 23%

Reagents, catalysts & solvents 2

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

Procedure

2-[[(E)-2-(4-Bromophenyl)ethenylsulfonylamino]benzenesulfonamide (79 mg, 0.19 mmol), (2-tert-butyl-1-ethynyl)diisopropoxyborane (80 mg, 0.38 mmol), (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (7.79 mg, 9.47 μmol) and sodium carbonate (40.1 mg, 0.38 mmol) were suspended in N,N-dimethylformamide (2.5 mL) and water (0.2 mL) and the reaction mixture was stirred vigorously under an atmosphere of argon at 90° C. for 3 hours. The mixture was filtered through a pad of Celite, the solvent was removed in vacuo and the residue was purified by preparative HPLC to give 10 mg (23% yield) of the title compound.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. customthe solvent was removed in vacuo
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-53048b30edc145859f09ad14ba5bded8
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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