Potassium Phosphate, Tribasic → (2'-Methyl-[2,4'-bipyridin]-5-yl)methanamine

HRID 711227Notes

Reaction equation

HRID 711227 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6](B(O)O)[CH:5]=[CH:4][N:3]=1.Cl[C:12]1[N:17]=[CH:16][C:15]([CH2:18][NH2:19])=[CH:14][CH:13]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([C:12]2[CH:13]=[CH:14][C:15]([CH2:18][NH2:19])=[CH:16][N:17]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 41926642-Methylpyridine-4-boronic acidHCID 70209275-(Aminomethyl)-2-chloropyridine

Product 1

HCID 67208679(2'-Methyl-[2,4'-bipyridin]-5-yl)methanamine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
96 °C

Procedure

A mixture of (2-methylpyridin-4-yl)boronic acid 15-1 (476 mg, 3.48 mmol), (6-chloropyridin-3-yl)methanamine 18-1 (496 mg, 3.48 mmol), Pd(PPh3)4 (202 mg, 0.175 mmol) and K3PO4 (1113 mg, 5.25 mmol) in dioxane (5 mL) was stirred at 96° C. under argon overnight. After cooling to room temperature, the mixture was filtered through celite and washed with ethyl acetate. The filtrate was concentrated by rotavap and the residue subjected to silica gel column chromatography with 7% ammonia-saturated methanol in dichloromethane as eluent to give (2′-methyl-[2,4′-bipyridin]-5-yl)methanamine 18-2 as an oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered through celite
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated by rotavap

Sources & evidence

ORD record
ord-d158a4e1e6714eda8406e76690313d19
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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