Potassium Carbonate → HCID 21959550, compound

HRID 2247249Notes

Reaction equation

HRID 2247249 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([CH3:14])([CH3:13])[CH3:12].[N:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>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.C1(C)C=CC=CC=1>[C:11]([C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[C:18]1[CH:19]=[CH:20][N:15]=[CH:16][CH:17]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2385872-Bromo-1-tert-butyl-4-nitrobenzeneHCID 2734379(Pyridin-4-yl)boronic acid

Product 1

HCID 21959550HCID 21959550, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-bromo-1-tert-butyl-4-nitrobenzene (8.6 g, 33.3 mmol) and toluene (70 mL) in a 150 mL round bottom flask, 4-pyridylboronic acid (4.5 g, 36.6 mmol), Pd(PPh3)4 (3.8 g, 3.3 mmol) and K2CO3 (13.8 g, 99.9 mmol) were added. The solution was stirred for 24 h at 80° C. before cooling to RT. The solution was filtered through a pad of Celite® and purified by silica flash chromatography (30% EtOAc/Hexanes). This afforded the desired compound as a yellow solid. MS (ES+):257.2 (M+H)+; (ES−):255.2 (M−H)−. Calc'd for C15H16N2O2:256.12.

Workup

  1. temperaturebefore cooling to RT
  2. filtrationThe solution was filtered through a pad of Celite®
  3. custompurified by silica flash chromatography (30% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-ea376d8c975a47e0843d36f1dc8b1cf9
Source dataset
uspto-grants-2010_03
Patent number
US07687643B2

Reaction notes

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