Sodium Carbonate → HCID 9902355, compound

HRID 2214930Notes

Reaction equation

HRID 2214930 reaction equation
Br[C:2]1[C:3]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[N:4][N:5]2[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:6]=12.[F:20][C:21]1[CH:26]=[C:25](B(O)O)[CH:24]=[CH:23][N:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:3]2[C:2]([C:25]3[CH:24]=[CH:23][N:22]=[C:21]([F:20])[CH:26]=3)=[C:6]3[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH3:12])[N:5]3[N:4]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27833962-Fluoropyridine-4-boronic acidHCID 21948673HCID 21948673, compound

Product 1

HCID 9902355HCID 9902355, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-bromo-2-(4-fluorophenyl)-7-methoxypyrazolo[1,5-a]pyridine (from Example 27,180 mg, 0.560 mmol), 2-fluoropyridin-4-ylboronic acid (from Example 33, 112 mg, 0.800 mmol) and dichlorobis(triphenylphosphine)palladium (40.0 mg, 0.056 mmol) in N,N-dimethylformamide (6.00 mL) was placed in a pre-heated oil bath at 110° C. To the reaction was added, in a dropwise manner, 2M sodium carbonate (0.840 mL, 1.68 mmol). The reaction was allowed to stir for three hours before cooling to room temperature and filtering through a Celite 545 pad. The Celite filter was washed with ethyl acetate and the filtrate was concentrated to dryness at 50° C. under vacuum. The residue was dissolved in methylene chloride and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated and purified by silica gel chromatography to yield the title compound (110 mg, 0.326 mmol, 58%). 1H NMR (CDCl3): δ 8.14(d, 1H, J=5.5 Hz), 7.53(dd, 2H, J=6.0, 8.0 Hz), 7.24–7.32(m, 2H), 7.00–7.10(m, 3H), 6.89(s, 1H), 6.23(dd, 1H, J=2.0, 6.0 Hz), 4.2(s, 3H). MS (ES+ve): 338.1 (40, M+), 323.1 (100).

Workup

  1. customwas placed in a pre-heated oil bath at 110° C
  2. filtrationfiltering through a Celite 545 pad
  3. filtrationThe Celite filter
  4. washwas washed with ethyl acetate
  5. concentrationthe filtrate was concentrated to dryness at 50° C. under vacuum
  6. dissolutionThe residue was dissolved in methylene chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe drying agent was removed by filtration
  9. concentrationthe filtrate was concentrated
  10. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-311542651c1a49529531a6981209476e
Source dataset
uspto-grants-2006_09
Patent number
US07109209B2

Reaction notes

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