Cesium carbonate → HCID 136123737, compound

HRID 1850348Notes

Reaction equation

HRID 1850348 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([C:6]2[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[OH:18])=[N:8][CH:9]=[CH:10][N:11]=2)[CH2:3]1.Cl[C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[CH:29][C:20]=1[N:2]1[CH2:5][CH:4]([C:6]2[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[OH:18])=[N:8][CH:9]=[CH:10][N:11]=2)[CH2:3]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 119282-ChloroquinolineHCID 136359919HCID 136359919, compound

Product 1

HCID 136123737HCID 136123737, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-(3-azetidin-3-yl-pyrazin-2-yl)-phenol hydrochloride (275 mg, 1 mmol) and 2-chloro-quinoline (163 mg, 1 mmol) in DMF (10 mL) was added Cs2CO3 (650 mg, 2 mmol). The reaction mixture was stirred at 100° 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 ISCO silica gel column (10% to 80% EtOAc in petroleum ether) to give 2-[3-(1-quinolin-2-yl-azetidin-3-yl)-pyrazin-2-yl]-phenol (56 mg, 0.16 mmol, yield 16%).

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 ISCO silica gel column (10% to 80% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-837be894edae4359881d3a92fa9a8703
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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