Cesium carbonate → HCID 58546965, compound

HRID 1850354Notes

Reaction equation

HRID 1850354 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([C:6]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=3)=[N:10][CH:9]=[CH:8][N:7]=2)[CH2:3]1.Cl[C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1.[C:31]([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[CH3:19][O:18][C:14]1[CH:13]=[C:12]([C:11]2[C:6]([CH:4]3[CH2:5][N:2]([C:21]4[CH:30]=[CH:29][C:28]5[C:23](=[C:24]([CH3:31])[CH:25]=[CH:26][CH:27]=5)[N:22]=4)[CH2:3]3)=[N:7][CH:8]=[CH:9][N:10]=2)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 119282-ChloroquinolineHCID 67469066HCID 67469066, compound

Product 1

HCID 58546965HCID 58546965, compoundYield 63.35%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-azetidin-3-yl-3-(3-methoxy-phenyl)-pyrazine hydrochloride (138 mg, 0.50 mmol) and 2-chloro-quinoline (84 mg, 0.50 mmol) in DMF (6 mL) was added Cs2CO3 (325 mg, 1.0 mmol). The reaction mixture was stirred at 110° C. overnight. The reaction mixture was diluted with water, extracted with EtOAc (30 mL×2). The combined organic extracts were washed with water (30 mL) and brine (30 mL), dried over Na2SO4 and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (20% to 40% EtOAc in petroleum ether) to give 2-{3-[3-(3-methoxy-phenyl)-pyrazin-2-yl]-azetidin-1-yl}-8-methyl-quinoline (118 mg, 0.31 mmol, 63.35%).

Workup

  1. extractionextracted with EtOAc (30 mL×2)
  2. washThe combined organic extracts were washed with water (30 mL) and brine (30 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by flash column chromatography on silica gel (20% to 40% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-93ef3a46a42f4c869577d3580e512791
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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