Cesium carbonate → HCID 67367419, compound

HRID 1676184Notes

Reaction equation

HRID 1676184 reaction equation
Cl.[F:2][C:3]1[CH:8]=[C:7]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:6]=[CH:5][C:4]=1[N:13]1[CH:18]=[CH:17][C:16]([O:19][CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:15][C:14]1=[O:26].[Br:27][C:28]1[CH:29]=[N:30][C:31](Cl)=[N:32][CH:33]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[Br:27][C:28]1[CH:29]=[N:30][C:31]([N:23]2[CH2:24][CH2:25][CH:20]([O:19][C:16]3[CH:17]=[CH:18][N:13]([C:4]4[CH:5]=[CH:6][C:7]([S:9]([CH3:12])(=[O:11])=[O:10])=[CH:8][C:3]=4[F:2])[C:14](=[O:26])[CH:15]=3)[CH2:21][CH2:22]2)=[N:32][CH:33]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 6066655-Bromo-2-chloropyrimidineHCID 67368299HCID 67368299, compound

Product 1

HCID 67367419HCID 67367419, compoundYield 53.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 1-(2-fluoro-4-(methylsulfonyl)phenyl)-4-(piperidin-4-yloxy)pyridin-2(1H)-one hydrochloride (100 mg, 0.248 mmol, prepared according to the procedures described in Example 9), 5-bromo-2-chloropyrimidine (144 mg, 0.745 mmol) and cesium carbonate (324 mg, 0.993 mmol) in DMF (3 mL) was placed in a microwave and heated at 160° C. for 20 min. The reaction mixture was diluted with EtOAc (30 mL) and washed with water 3 times. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to give a crude yellow solid. The residue was purified by flash chromatography (SiO2, 0-100% EtOAc/Hexanes) to give a white solid (70 mg, 53.9%). MS (ESI) 523 (M+H).

Workup

  1. customprepared
  2. washwashed with water 3 times
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto give a crude yellow solid
  6. customThe residue was purified by flash chromatography (SiO2, 0-100% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-125f2c65f98f42dfb650fcb6f8629c42
Source dataset
uspto-grants-2011_08
Patent number
US08003796B2

Reaction notes

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