Potassium Phosphate, Tribasic → 5'-Methoxy-5-morpholino-2,3'-bipyridin-3-amine

HRID 1431583Notes

Reaction equation

HRID 1431583 reaction equation
Cl[C:2]1[C:7]([NH2:8])=[CH:6][C:5]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:4][N:3]=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[N:21][CH:22]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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].O.O1CCOCC1>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([C:2]2[C:7]([NH2:8])=[CH:6][C:5]([N:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)=[CH:4][N:3]=2)[CH:20]=[N:21][CH:22]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 27630875-Methoxypyridine-3-boronic AcidHCID 596310392-Chloro-5-morpholinopyridin-3-amine

Product 1

HCID 596313095'-Methoxy-5-morpholino-2,3'-bipyridin-3-amine

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

2-Chloro-5-morpholinopyridin-3-amine (0.26 g, 1.2 mmol), 5-methoxypyridin-3-ylboronic acid (0.24 g, 1.6 mmol), tricyclohexylphosphine (42.7 mg, 0.15 mmol), and tris(dibenzylideneacetone)dipalladium (0) (68.4 mg, 0.075 mmol) were added to a flask then degassed and backfilled with argon. To the flask, 1,4-dioxane (5.0 mL) and aq. 1.3M potassium phosphate tribasic (2.3 mL, 3 mmol) were added by syringe. The resulting reaction was heated to 90° C. and monitored with TLC and LC-MS. After 19 h, the reaction was cooled to rt then poured into water. After extracting twice with EtOAc and twice with DCM, the combined organic extractions were dried over anhydrous magnesium sulfate. After filtration and concentration, the residue was purified on basic alumina (0-100% EtOAc in hexanes) to afford a brown solid as 5′-methoxy-5-morpholino-2,3′-bipyridin-3-amine. Mass Spectrum (pos.) m/e: 287.2 (M+1).

Workup

  1. customthen degassed
  2. customThe resulting reaction
  3. temperaturethe reaction was cooled to rt
  4. extractionAfter extracting twice with EtOAc and twice with DCM
  5. extractionthe combined organic extractions
  6. dry with materialwere dried over anhydrous magnesium sulfate
  7. filtrationAfter filtration and concentration
  8. customthe residue was purified on basic alumina (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-162e5d7f851049d29b3dbd3f52cc2f76
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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