Cesium carbonate → HCID 59351380, compound

HRID 887478Notes

Reaction equation

HRID 887478 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:8]1[C:9]([CH:14]2[CH2:19][CH2:18][N:17]([C:20](=[O:22])[CH3:21])[CH2:16][CH2:15]2)=[N:10][CH:11]=[CH:12][N:13]=1.[Cl:23][C:24]1[N:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1>CN1C(=O)CCC1>[Cl:23][C:24]1[N:29]=[CH:28][C:27]([O:30][C:8]2[C:9]([CH:14]3[CH2:19][CH2:18][N:17]([C:20](=[O:22])[CH3:21])[CH2:16][CH2:15]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 8198212-Chloro-5-hydroxypyridineHCID 59351377HCID 59351377, compound

Product 1

HCID 59351380HCID 59351380, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

To a mixture of cesium carbonate (0.505 g, 1.55 mmol), 1-(4-(3-chloropyrazin-2-yl)piperidin-1-yl)ethanone (0.129 g, 0.538 mmol), and 6-chloropyridin-3-ol (0.140 g, 1.08 mmol) was added NMP (2 mL). The reaction mixture was degassed and heated to 130° C. for 2 h. The reaction mixture was diluted with EtOAc. The organic phase was washed with water (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (50% to 100% EtOAc (10% MeOH) in hexanes) gave 1-(4-(3-(6-chloropyridin-3-yloxy)pyrazin-2-yl)piperidin-1-yl)ethanone as a colorless oil that was used in the next step without further purification. MS (ESI, pos. ion) m/z: 333.2 (M+1).

Workup

  1. customThe reaction mixture was degassed
  2. additionThe reaction mixture was diluted with EtOAc
  3. washThe organic phase was washed with water (1×), brine (1×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography on silica gel (50% to 100% EtOAc (10% MeOH) in hexanes)

Sources & evidence

ORD record
ord-38e83fc99de546fb9a2b3e8d080cb75e
Source dataset
uspto-grants-2012_08
Patent number
US08247418B2

Reaction notes

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