Cesium carbonate → HCID 17755530, compound

HRID 1294068Notes

Reaction equation

HRID 1294068 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH2:11])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].[C:18]([O:22][C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>CN(C=O)C>[N+:8]([C:5]1[C:4]([NH2:11])=[CH:3][C:2]([O:32][C:29]2[CH:28]=[CH:27][C:26]([NH:25][C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:24])=[CH:31][CH:30]=2)=[CH:7][N:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2756771N-Boc-4-hydroxyanilineHCID 589057095-Bromo-2-nitropyridin-3-amine

Product 1

HCID 17755530HCID 17755530, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5-bromo-2-nitropyridine-3-ylamine (436 mg, 2.0 mmol) in DMF (10 mL) was added Cs2CO3 (977 mg, 3.0 mmol) followed by 4-(t-butoxycarbonyl)aminophenol (459 mg, 2.2 mmol) in DMF (10 mL) at 0° C. then stirred at room temperature for 3 days. The mixture was extracted with ethyl acetate. The organic layer was washed with NaHCO3 (aq) and brine, dried over Na2SO4 then evaporated. Sequence purification on SiO2 column chromatography gave the title compound (624.2 mg, 90%): MS m/e 347 (M+1).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with NaHCO3 (aq) and brine
  3. dry with materialdried over Na2SO4
  4. customthen evaporated
  5. customSequence purification on SiO2 column chromatography

Sources & evidence

ORD record
ord-f95f5af022104ce8a19b8000816e7764
Source dataset
uspto-grants-2007_07
Patent number
US07238813B2

Reaction notes

Loading…