Sodium Carbonate → 3-(3,6-dihydro-2H-thiopyran-4-yl)-2-fluoropyridine

HRID 410316Notes

Reaction equation

HRID 410316 reaction equation
FC(F)(F)S(O[C:7]1[CH2:8][CH2:9][S:10][CH2:11][CH:12]=1)(=O)=O.[F:15][C:16]1[C:21](B(O)O)=[CH:20][CH:19]=[CH:18][N:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.O.CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[S:10]1[CH2:11][CH:12]=[C:7]([C:21]2[C:16]([F:15])=[N:17][CH:18]=[CH:19][CH:20]=2)[CH2:8][CH2:9]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 226257513,6-Dihydro-2H-thiopyran-4-yl trifluoromethanesulfonate

Product 1

HCID 593271023-(3,6-dihydro-2H-thiopyran-4-yl)-2-fluoropyridine

Reagents, catalysts & solvents 3

HCID 178424406HCID 178424406, compoundCatalystHCID 962WaterSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
135 °C

Procedure

A mixture of 3,6-dihydro-2H-thiopyran-4-yl trifluoromethanesulfonate (4.0 g, 16.11 mmol), 2-fluoropyridin-3-ylboronic acid (2.498 g, 17.72 mmol), sodium carbonate (5.12 g, 48.3 mmol), and dichlorobis(tri-o-tolylphosphine)palladium(ii) (0.633 g, 0.806 mmol) in p-dioxane/H2O (10:1, 22 mL) was heated at 135° C. in 30 min. by microwave. The reaction mixture was cooled, diluted with H2O, extracted with EtOAc (3×), dried over MgSO4, concentrated and purified by ISCO (0-40% EtOAc/Hexanes) to give the expected product was a light brown oil. MS (M+1): 196.2.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with EtOAc (3×)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. custompurified by ISCO (0-40% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-87013de6c6b54685b43ee908202d6f44
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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