Potassium Phosphate, Tribasic → HCID 67486552, compound

HRID 1972167Notes

Reaction equation

HRID 1972167 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH3:15])=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[C:16](=[O:23])([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[NH2:17].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:15][C:10]1[C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:17][C:16](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:7]=2)=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 77922tert-Butyl carbamateHCID 22442122HCID 22442122, compound

Product 1

HCID 67486552HCID 67486552, compoundYield 83.7%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

3-(2-Chloropyridin-4-yloxy)-2-methylpyridine (4.8 g, 21.8 mmol), tert-butyl carbamate (6.37 g, 54.4 mmol), and potassium phosphate (5.08 g, 23.9 mmol) were added to degassed toluene (100 mL). 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (0.944 g, 1.63 mmol), tris(dibenzylideneacetone)-dipalladium (0.996 g, 1.09 mmol) and degassed water (25 mL) were added, and the reaction was stirred at 90° C. for 3 days. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried, concentrated, and flash chromatographed (10-50% ethyl acetate/hexanes) to give the title compound (5.5 g, 59% yield) as a light yellow solid.

Workup

  1. customto degassed toluene (100 mL)
  2. additionwere added
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customflash chromatographed (10-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f489cbc3183c4371b78d83aae28bc544
Source dataset
uspto-grants-2013_04
Patent number
US08431713B2

Reaction notes

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