Sodium Bicarbonate → HCID 21075865, compound

HRID 1374157Notes

Reaction equation

HRID 1374157 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[N:9][CH:10]=[C:11]([Cl:13])[CH:12]=1)(=O)=O.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].[F:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42](I)[C:41]=1[C:47]1[N:48]=[N:49][N:50]([CH3:52])[N:51]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:13][C:11]1[CH:10]=[N:9][CH:8]=[C:7]([C:42]2[CH:43]=[CH:44][CH:45]=[C:40]([F:39])[C:41]=2[C:47]2[N:48]=[N:49][N:50]([CH3:52])[N:51]=2)[CH:12]=1

Participants

8

Reactant 5

HCID 516892Sodium BicarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 151858705-Chloropyridin-3-yl trifluoromethanesulfonateHCID 161029015-(2-Fluoro-6-iodophenyl)-2-methyl-2H-tetrazole

Product 1

HCID 21075865HCID 21075865, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-chloropyridin-3-yl trifluoromethanesulfonate (6.00 g, 22.9 mmol), bis(pinacolato)diboron (6.12 g, 24.1 mmol), potassium acetate (6.75 g, 68.8 mmol), and [1,1′-bis-(diphenylphosphino)ferrocene]palladium(II) dichloride (0.60 g, 0.82 mmol) in 30 mL DMF was heated to 80° C. under N2 for 2 hours. The reaction mixture was cooled to room temperature, and 5-(2-fluoro-6-iodophenyl)-2-methyl-2H-tetrazole (4.88 g, 16.1 mmol), sodium bicarbonate (2M, 34.4 mL, 68.8 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (0.60 g, 0.82 mmol) were added. The reaction mixture was heated to 80° C. overnight, then cooled to room temperature and partitioned between ethyl acetate and water. The organic extract was washed with water and brine, dried over Na2SO4, filtered and concentrated under vacuum. The residue was subjected to silica gel chromatography eluted with 0–30% ethyl acetate in hexanes to provide 3-chloro-5-[3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)phenyl]pyridine that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 290.11 for M+H+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. temperatureThe reaction mixture was heated to 80° C. overnight
  3. temperaturecooled to room temperature
  4. custompartitioned between ethyl acetate and water
  5. extractionThe organic extract
  6. washwas washed with water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. washeluted with 0–30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-e81b485628114c8f8dc3941b4f58b8c8
Source dataset
uspto-grants-2007_01
Patent number
US07163951B2

Reaction notes

Loading…