Cesium carbonate → HCID 66721121, compound

HRID 244061Notes

Reaction equation

HRID 244061 reaction equation
[Cl:1][C:2]1[C:3]([C:9]2[C:10]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([OH:26])[CH:20]=3)=[N:11][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:14]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl.Cl[CH2:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[C:3]([C:9]2[C:10]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([O:26][CH2:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33])[CH:20]=3)=[N:11][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:14]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 66840842HCID 66840842, compound

Product 1

HCID 66721121HCID 66721121, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2 g (4.88 mmol) of methyl 3,5-dichloro-2′-(4-chloro-3-hydroxyphenyl)-2,3′-bipyridine-6′-carboxylate in 20 mL of anhydrous DMF placed under argon are added 1.15 g (7.32 mmol) of 3-chloro-N,N-dimethylpropane-1-amine hydrochloride and 4.77 g (14.64 mmol) of cesium carbonate. The reaction medium is stirred for 18 hours at 90° C., cooled to room temperature and then concentrated under reduced pressure. The residue is taken up in 250 mL of EtOAc and washed with 250 mL of aqueous 5% Na2CO3 solution and then with 100 mL of water. After drying over Na2SO4 and concentrating under reduced pressure, the residue is purified by chromatography on a column of silica gel, eluting with a DCM/methanol gradient of from 0 to 15% methanol. After concentrating under reduced pressure, 1.82 g of methyl 3,5-dichloro-2′-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-2,3′-bipyridine-6′-carboxylate is obtained in the form of a gum.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. washwashed with 250 mL of aqueous 5% Na2CO3 solution
  4. dry with materialAfter drying over Na2SO4
  5. concentrationconcentrating under reduced pressure
  6. customthe residue is purified by chromatography on a column of silica gel
  7. washeluting with a DCM/methanol gradient of from 0 to 15% methanol
  8. concentrationAfter concentrating under reduced pressure

Sources & evidence

ORD record
ord-87981415cf564b1b88ce8d998ec4f5d2
Source dataset
uspto-grants-2014_02
Patent number
US08653276B2

Reaction notes

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