Cesium carbonate → HCID 59686984, compound

HRID 606326Notes

Reaction equation

HRID 606326 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:18]1[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[N:22][CH:23]=1>CN(C)C=O>[N+:24]([C:21]1[N:22]=[CH:23][C:18]([O:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=2)=[CH:19][CH:20]=1)([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 650524-HydroxybenzamideHCID 8176205-Bromo-2-nitropyridine

Product 1

HCID 59686984HCID 59686984, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-hydroxybenzamide (150 mg, 1.1 mmol) and caesium carbonate (394 mg, 1.21 mmol) was dissolved in dimethylformamide (7 ml). 5-bromo-2-nitropyridine (244 mg, 1.21 mmol) was then added. The mixture was left at 50 degrees until the starting material was consumed according to TLC (1% methanol in ether). Purification by flash chromatography yielded 4-[(6-nitro-3-pyridinyl)oxy]benzamide (110 mg, 38%)

Workup

  1. waitThe mixture was left at 50 degrees until the starting material
  2. customwas consumed
  3. customPurification by flash chromatography

Sources & evidence

ORD record
ord-89b6d877c8824540902fa7d674b1bc09
Source dataset
uspto-grants-2011_03
Patent number
US07915295B2

Reaction notes

Loading…