Sodium Carbonate → HCID 57582324, compound

HRID 1094807Notes

Reaction equation

HRID 1094807 reaction equation
I[C:2]1[C:3]([NH2:9])=[N:4][C:5]([NH2:8])=[CH:6][CH:7]=1.[F:10][C:11]1[CH:12]=[CH:13][C:14]([O:20][CH2:21][CH2:22][CH3:23])=[C:15](B(O)O)[CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C(O)C.O.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.[Pd].CCCCCCC>[F:10][C:11]1[CH:16]=[CH:15][C:14]([O:20][CH2:21][CH2:22][CH3:23])=[C:13]([C:2]2[C:3]([NH2:9])=[N:4][C:5]([NH2:8])=[CH:6][CH:7]=2)[CH:12]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 4762183-Iodopyridine-2,6-diamineHCID 16217217(5-Fluoro-2-propoxyphenyl)boronic acid

Product 1

HCID 57582324HCID 57582324, compoundYield 35.5%

Reagents, catalysts & solvents 4

HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8900HeptaneSolvent

Procedure

To a suspension of 3-iodopyridine-2,6-diamine (Preparation 44, 1.5 g, 6.38 mmol) in ethanol (5 ml) and water (5 ml) was added 5-fluoro-2-propoxyphenyl boronic acid (1.6 g, 8.10 mmol) and sodium carbonate (744 mg, 7.02 mmol), then the slurry was stirred for 10 minutes at room temperature under nitrogen. Palladium (0) bis(dibenzylideneacetone) (0.088 g, 0.153 mmol) and tri-tert-butyl phosphine (1M solution in toluene, 1.28 ml, 1.28 mmol) were added and the reaction was heated at 80° C. for 6 hours before concentrating in vacuo. The residue was taken up in ethyl acetate (100 ml) and washed with water (3×50 ml) then brine (50 ml) before drying over anhydrous MgSO4, filtering and concentrating in vacuo. The residue was purified by column chromatography eluting with 1:9 to 8:2 ethyl acetate:heptane to afford the title compound as a yellow foam (0.591 g, 35% yield).

Workup

  1. temperaturethe reaction was heated at 80° C. for 6 hours
  2. concentrationbefore concentrating in vacuo
  3. washwashed with water (3×50 ml)
  4. dry with materialbrine (50 ml) before drying over anhydrous MgSO4
  5. filtrationfiltering
  6. concentrationconcentrating in vacuo
  7. customThe residue was purified by column chromatography
  8. washeluting with 1:9 to 8:2 ethyl acetate

Sources & evidence

ORD record
ord-b4965e2b23a6489f98ceb7d36e2dc40f
Source dataset
uspto-grants-2012_03
Patent number
US08134007B2

Reaction notes

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