3-Nitrophenylboronic Acid → HCID 66955149, compound

HRID 1615374Notes

Reaction equation

HRID 1615374 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[N+:17]([C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1)([O-:19])=[O:18].C(OCC)(=O)C>CN(C=O)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[N+:17]([C:20]1[CH:25]=[C:24]([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[CH:7][NH:8]3)=[CH:4][CH:3]=2)[CH:23]=[CH:22][CH:21]=1)([O-:19])=[O:18]

Participants

8

Reactant 4

HCID 16773-Nitrophenylboronic AcidHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 6764936-Bromoindole

Product 1

HCID 66955149HCID 66955149, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

6-Bromo-1H-indole (1.00 g, 5.10 mmol) and potassium carbonate (1.41 g, 10.2 mmol) were dissolved in a DMF/water (4:1, 10 mL) mixture solution, and then the gas included in the mixture solution was removed using ultrasonic wave and nitrogen gas. After sequentially adding 3-nitrophenylboronic acid (853 mg, 5.61 mmol) and Pd(dppf)Cl2 (416 mg, 0.51 mmol), the mixture was stirred at room temperature in a sealed reactor. 2 hours later, after adding ethyl acetate and water, the reaction solution was filtered through a diatomite pad. The organic layer was separated from the filtrate and the aqueous layer was extracted with ethyl acetate. The combined organic layer was dried with anhydrous magnesium sulfate and then concentrated. Purification of the residue by chromatography (silica gel, EA:Hx=1:4) yielded the target compound as white solid.

Workup

  1. customwas removed
  2. filtrationthe reaction solution was filtered through a diatomite pad
  3. customThe organic layer was separated from the filtrate
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. dry with materialThe combined organic layer was dried with anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customPurification of the residue by chromatography (silica gel, EA:Hx=1:4)

Sources & evidence

ORD record
ord-da85d6f9a7f64064a303ace93376a3d2
Source dataset
uspto-grants-2014_07
Patent number
US08765749B2

Reaction notes

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