Cesium carbonate → HCID 58548420, compound

HRID 1842526Notes

Reaction equation

HRID 1842526 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([C:6]2[CH:15]=[CH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]=2)[CH2:3]1.C([O-])([O-])=O.[Cs+].[Cs+].[Br:22][C:23]1[C:24](F)=[N:25][CH:26]=[CH:27][CH:28]=1>CN(C=O)C.O>[Br:22][C:23]1[C:24]([N:2]2[CH2:3][CH:4]([C:6]3[CH:15]=[CH:14][C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[N:7]=3)[CH2:5]2)=[N:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27627783-Bromo-2-fluoropyridineHCID 67469184HCID 67469184, compound

Product 1

HCID 58548420HCID 58548420, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-azetidin-3-yl-quinoline hydrochloride (1.70 g, 7.75 mmol) in DMF (30 mL) at room temperature was added Cs2CO3 (5.2 g, 16 mmol) and 3-bromo-2-fluoro-pyridine (1.5 g, 9.0 mmol). The reaction mixture was heated to 90° C. overnight and then diluted with water (60 mL) and extracted with EtOAc (2×50 mL). The combined organic extracts were washed with water (60 mL) and brine (60 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (5% to 30% EtOAc in hexanes) to give the title product (1.50 g, 4.4 mmol, 58% yield) as a white solid.

Workup

  1. extractionextracted with EtOAc (2×50 mL)
  2. washThe combined organic extracts were washed with water (60 mL) and brine (60 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 (5% to 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9e299496969343d0ba2e3a5199060f8d
Source dataset
uspto-grants-2015_02
Patent number
US08946230B2

Reaction notes

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