Potassium Phosphate, Tribasic → 6-Methoxy[3,4'-bipyridin]-5-amine

HRID 1628218Notes

Reaction equation

HRID 1628218 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[N:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[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]>[CH3:9][O:8][C:5]1[C:4]([NH2:10])=[CH:3][C:2]([C:14]2[CH:15]=[CH:16][N:11]=[CH:12][CH:13]=2)=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2734379(Pyridin-4-yl)boronic acidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 447548695-Bromo-2-methoxypyridin-3-amine

Product 1

HCID 139424726-Methoxy[3,4'-bipyridin]-5-amineYield 74%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
110 °C

Procedure

To a flask were weighed 5-bromo-2-methoxypyridin-3-amine, 11.1.A, (1 g, 4.9 mmol), pyridin-4-ylboronic acid (0.73 g, 5.9 mmol), X-Phos (0.47 g, 0.99 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.22 g, 0.25 mmol), and Potassium phosphate tribasic (3.13 g, 14.8 mmol). N-butanol was added as a solvent and the reaction mixture was heated at 110° C. for 3 hr. The solids were filtered off through a pad of celite. The filtrate was concentrated and chromatographed by gradient EtOAc/DCM and then 10% MeOH/DCM to afford 730 mg of 11.1.B (74%).

Workup

  1. customTo a flask were weighed
  2. filtrationThe solids were filtered off through a pad of celite
  3. concentrationThe filtrate was concentrated
  4. customchromatographed by gradient EtOAc/DCM

Sources & evidence

ORD record
ord-15c5780ec2ea4453ab6dbf71b7bcc3e3
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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