Cesium carbonate → 1253911-35-1

HRID 1431065Notes

Reaction equation

HRID 1431065 reaction equation
Br.[NH2:2][C:3]1[N:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.Cl[CH2:11][C:12]([CH3:15])([OH:14])[CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[NH2:2][C:3]1[N:8]=[CH:7][C:6]([O:9][CH2:11][C:12]([CH3:15])([OH:14])[CH3:13])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 684091-Chloro-2-methylpropan-2-olHCID 667434106-Aminopyridin-3-ol--hydrogen bromide (1/1)

Product 1

HCID 667489771253911-35-1

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a microwave flask containing 6-aminopyridin-3-ol hydrobromide (700 mg, 3.66 mmol) and 1-chloro-2-methyl-2-propanol (597 mg, 5.5 mmol) in anhydrous dimethylformamide (17 ml) was added cesium carbonate (3.7 g, 11.4 mmol) and the material was heated in a microwave oven at 140° C. for 3 hours. The vial was cooled to ambient and the solvent was concentrated in vacuo (rotary evaporator/mechanical pump). The residue was taken up in methylene chloride and filtered to remove insolubles, rinsing well with methylene chloride. The crude material was purified by HPLC on silica gel, eluting with a gradient of 2% to 10% methanol/methylene chloride to provide the desired product as a orange-brown viscous oil which solidified on standing (449 mg). MS (H+)=183 m/e.

Workup

  1. temperatureThe vial was cooled to ambient and the solvent
  2. concentrationwas concentrated in vacuo (rotary evaporator/mechanical pump)
  3. filtrationfiltered
  4. customto remove insolubles
  5. washrinsing well with methylene chloride
  6. customThe crude material was purified by HPLC on silica gel
  7. washeluting with a gradient of 2% to 10% methanol/methylene chloride

Sources & evidence

ORD record
ord-2094ead4367f4844a45879d026029966
Source dataset
uspto-grants-2015_01
Patent number
US08940741B2

Reaction notes

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