Cesium carbonate → HCID 86683725, compound

HRID 1026439Notes

Reaction equation

HRID 1026439 reaction equation
Cl.[CH3:2][N:3]1[CH:8]2[CH2:9][O:10][CH2:11][CH:4]1[CH2:5][NH:6][CH2:7]2.Br[C:13]1[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[N:17][CH:18]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[CH3:2][N:3]1[CH:8]2[CH2:9][O:10][CH2:11][CH:4]1[CH2:5][N:6]([C:13]1[CH:18]=[N:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)[CH2:7]2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 8176205-Bromo-2-nitropyridineHCID 67212441HCID 67212441, compound

Product 1

HCID 86683725HCID 86683725, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 112h (800 mg, 5.6 mmol) and 5-bromo-2-nitropyridine (1.37 g, 6.86 mmol) in DMSO (50 ml) was added Cs2CO3 (5g) and t-BuNH4I (cat.). The reaction mixture was stirred at 120° C. overnight. Then it was cooled to room temperature, and extracted with EtOAc (300 ml). The organic layer was washed with water (3×100 ml) and brine (150 ml), dried over Na2SO4, filtered and concentrated to get crude product, which was purified through a silica gel column eluting with DCM:MeOH=100:1 to 50:1 to give 112i as a yellow solid (850 mg, 72%) MS: [M+H]+: 265

Workup

  1. temperatureThen it was cooled to room temperature
  2. extractionextracted with EtOAc (300 ml)
  3. washThe organic layer was washed with water (3×100 ml) and brine (150 ml)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto get crude product, which
  8. customwas purified through a silica gel column
  9. washeluting with DCM

Sources & evidence

ORD record
ord-260999096eea45d6b6c49917b5ba88fe
Source dataset
uspto-grants-2014_05
Patent number
US08729072B2

Reaction notes

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