Phenylboronic Acid → HCID 69254862, compound

HRID 746780Notes

Reaction equation

HRID 746780 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][C:12]=2[NH:13][S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:4][CH:3]=1.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+].O>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>[C:2]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][C:12]=2[NH:13][S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 66827Phenylboronic AcidHCID 2735133Sodium Carbonate MonohydrateHCID 53421842N-[2-(4-Bromophenyl)thiophen-3-yl]propane-2-sulfonamide

Product 1

HCID 69254862HCID 69254862, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Heat in a sealed tube with stirring propane-2-sulfonic acid [2-(4-bromo-phenyl)-thiophen-3-yl]-amide (0.5 mmol), phenyl boronic acid (0.75 mmol), 2M Na2CO3 water solution (0.2 mL) and Pd(PPh3)4(0.05 mmol) in 4.0 ml of an anhydrous and deoxygenated 2:1 DME/EtOH mixture to 80° C.-100° C. for 24 h. Filter mixture through a small silica pad and elute with EtOAc. Evaporate the filtrate. Purify the product by flash chromatography (Silica gel-hexane/EtOAc) to obtain the title compound. MS (ES−): 356 (M−1).

Workup

  1. customdeoxygenated 2:1 DME/EtOH mixture to 80° C.-100° C. for 24 h
  2. filtrationFilter mixture through a small silica pad
  3. washelute with EtOAc
  4. customEvaporate the filtrate
  5. customPurify the product by flash chromatography (Silica gel-hexane/EtOAc)

Sources & evidence

ORD record
ord-ea08a19610ff4673b8e57e95f2e2ef95
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

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