Cesium carbonate → HCID 67497417, compound

HRID 1628224Notes

Reaction equation

HRID 1628224 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.[N:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:7]([O:6][C:5]1[CH:14]=[CH:15][C:2]([C:22]2[CH:23]=[CH:24][N:19]=[CH:20][CH:21]=2)=[CH:3][C:4]=1[N+:16]([O-:18])=[O:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 112782421-(Benzyloxy)-4-bromo-2-nitrobenzene

Product 1

HCID 67497417HCID 67497417, compoundYield 109.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-((4-bromo-2-nitrophenoxy)methyl)benzene 13.B (1.40 g, 4.55 mmol) and pyridin-4-ylboronic acid (665 mg, 5.45 mmol, available from Aldrich) in DMF (10 mL) was added cesium carbonate (2.93 g, 9.0 mmol). The mixture was stirred overnight at 80° C. and then partitioned between AcOEt and water. The organic phase was concentrated to afford 4-(4-(benzyloxy)-3-nitrophenyl)pyridine 13.0 (1.52 g, 109% yield) which was used in the next step without any further purification.

Workup

  1. custompartitioned between AcOEt and water
  2. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-4f8e8a6154ac447fba5e40fe3e3469b5
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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